Phenylcarbamates, processes and intermediate products for their preparation and their use as pesticides and fungicides

ABSTRACT

Phenylcarbamates of the formula I ##STR1## where the substituents and the index have the following meanings: R is cyano, nitro, trifluoromethyl, halogen, alkyl or alkoxy; 
     m is 0, 1 or 2; 
     R 1  is alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, and, in the event that X is NR a , additionally hydrogen; 
     X is a direct bond, O or NR a  ; 
     R a  is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl; 
     R 2  is hydrogen, 
     substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, alkylcarbonyl or alkoxycarbonyl; 
     R 3  and R 4  independently of one another are hydrogen, cyano, nitro, hydroxyl, amino, halogen, hetaryloxy, hetarylthio, hetarylamino or N-hetaryl-N-alkylamino, and 
     R 5  is one of the groups mentioned under R 3  or a group CR d  ═NOR e  ; 
     processes and intermediates for their preparation, and their use.

This appln is a 371 of PCT/EP96/04575 filed on Oct. 22, 1996.

The present invention relates to phenylcarbamates of the formula##STR2## where the substituents and the index have the followingmeanings:

R is cyano, nitro, trifluoromethyl, halogen, C₁ -C₄ -alkyl or C₁ -C₄-alkoxy;

m is 0, 1 or 2, it being possible for the radicals R to be different ifn is 2;

R¹ is alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, and, in theevent that X is NR^(a), additionally hydrogen;

X is a direct linkage, O or NR^(a) ;

R^(a) is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl;

R² is hydrogen,

unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl,cycloalkenyl, cycloalkynyl, alkylcarbonyl or alkoxycarbonyl;

R³ and R⁴ independently of one another are

hydrogen, cyano, nitro, hydroxyl, amino, halogen,

C₁ -C₆ -alkyl, C₁ -C6-alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino,di-C₁ -C₆ -alkylamino, C₂ -C₆ -alkenyl, C₂ -C₆ -alkenyloxy, C₂ -C₆-alkenylthio, C₂ -C₆ -alkenylamino, N--C₂ -C₆ -alkenyl-N--C₁ -C₆-alkylamino, C₂ -C₆ -alkynyl, C₂ -C₆ -alkynyloxy, C₂ -C₆ -alkynylthio,C₂ -C₆ -alkynylamino, N--C₂ -C₆ -alkynyl-N--C₁ -C₆ -alkylamino, it beingpossible for the hydrocarbon radicals of these groups to be partially orfully halogenated and/or to have attached to them one to three of thefollowing radicals:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl,

C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl, C₁ -C₆-alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylsulfoxyl, C₁ -C₆ -alkoxy, C₁ -C₆-haloalkoxy, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆-alkylamino, di-C₁ -C₆ -alkylamino, C₂ -C₆ -alkenyloxy,

C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyloxy, heterocyclyl,heterocyclyloxy, aryl, aryloxy, aryl-C₁ -C₄ -alkoxy, arylthio, aryl-C₁-C₄ -alkylthio, hetaryl, hetaryloxy, hetaryl-C₁ -C₄ -alkoxy, hetarylthioand hetaryl- C₁ -C₄ -alkylthio, it being possible for the cyclicradicals, in turn, to be partially or fully halogenated and/or to haveattached to them one to three of the following groups: cyano, nitro,hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylsulfoxyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy,C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆-alkylamino, C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl,C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₂-C₆ -alkenyl, C₂ -C₆ -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy,arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR^(b))--A_(n)--R^(c) ;

C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyloxy, C₃ -C₆ -cycloalkylthio, C₃-C₆ -cycloalkylamino, N--C₃ -C₆ -cycloalkyl-N--C₁ -C₆ -alkylamino, C₅-C₈ -cycloalkenyl, C₅ -C₈ -cycloalkenyloxy, C₅ -C₈ -cycloalkenylthio, C₅-C₈ -cycloalkenylamino, N--C₅ -C₈ -cycloalkenyl-N--C₁ -C₆ -alkylamino,heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino,N-heterocyclyl-N--C₁ -C₆ -alkylamino, aryl, aryloxy, arylthio,arylamino, N-aryl-N--C₁ -C₆ -alkylamino, hetaryl, hetaryloxy,hetarylthio, hetarylamino, N-hetaryl-N--C₁ -C₆ -alkylamino, it beingpossible for the cyclic radicals to be partially or fully halogenatedand/or to have attached to them one to three of the following groups:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl,

C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylsulfoxyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkoxy-C₁-C₆ -alkyl, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆-alkylcarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆-alkylamino, C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl,

C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₂-C₆ -alkenyl, C₂ -C₆ -alkenyloxy, benzyl, aryl-C₁ -C₆ -alkoxy, aryl,aryloxy, hetaryl, hetaryloxy, it being possible for the cyclic radicalsof the six last-mentioned groups to be partially or fully halogenatedand/or to have attached to them a C₁ -C₆ -alkyl group;C(═NOR^(b))--A_(n) --R^(c) or NR^(f) --CO--D--R^(g) ;

A is oxygen, sulfur or nitrogen, the nitrogen having attached to ithydrogen or C₁ -C₆ -alkyl;

D is a direct linkage, oxygen or NR^(h) ;

n is 0 or 1;

R^(b) and R^(c) independently of one another are hydrogen or C₁ -C₆-alkyl;

R^(f) is hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆-alkynyl, C₁ -C₆ -alkoxy, C₂ -C₆ -alkenyloxy, C₂ -C₆ -alkynyloxy, C₁ -C₆-alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy and C₁ -C₆-alkoxycarbonyl;

R^(g), R^(h) independently of one another are hydrogen, C₁ -C₆ -alkyl,C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₃ -C₆-cycloalkenyl, aryl, aryl-C₁ -C₆ -alkyl, hetaryl and hetaryl-C₁ -C₆-alkyl;

R⁵ is one of the groups mentioned under R³ or a group CR^(d) ═NOR^(e) ;

R^(d) is one of the groups mentioned under R³ ;

R^(e) is hydrogen,

C₁ -C₁₀ -alkyl, C₃ -C₆ -cycloalkyl, C₂ -C₁₀ -alkenyl, C₂ -C₁₀ -alkynyl,C₁ -C₁₀ -alkylcarbonyl, C₂ -C₁₀ -alkenylcarbonyl, C₂ -C₁₀-alkynylcarbonyl or C₁ -C₁₀ -alkylsulfonyl, it being possible for theseradicals to be partially or fully halogenated and/or to have attached tothem one to three of the following groups:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl,

C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylsulfoxyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆-alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆-alkylamino, C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl,C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₂-C₆ -alkenyl, C₂ -C₆ -alkenyloxy, C₃ -C₆ -cycloalkyl, C₃ -C₆-cycloalkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl,aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it beingpossible for the last twelve groups mentioned, in turn, to be partiallyor fully halogenated and/or to have attached to them one to three of thefollowing groups:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl,

C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylsulfoxyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy,C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆-alkylamino, C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl,C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₂-C₆ -alkenyl, C₂ -C₆ -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy,arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR^(b))--A_(n) --R^(c);

aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl orhetarylsulfonyl, it being possible for these radicals to be partially orfully halogenated and/or to have attached to them one to three of thefollowing groups:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl,

C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylcarbonyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylsulfoxyl, C₃ -C₆ -cycloalkyl, C₁ -C₆-alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio,C₁ -C₆ -alkylamino, di-C₁ -C₆ -alkylamino, C₁ -C₆ -alkylaminocarbonyl,di-C₁ -C₆ -alkylaminocarbonyl, C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆-alkylaminothiocarbonyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkenyloxy, benzyl,benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR^(b))--A_(n)--R^(c),

and to their salts.

Furthermore, the invention relates to processes and intermediates forthe preparation of these compounds and to compositions comprising themfor controlling animal pests and harmful fungi.

Anilides for controlling harmful fungi are disclosed in the literature(WO-A 93/15046). Moreover, DE-A 44 41 674 (= WO 96/16030) describesanilides which act against animal pests and harmful fungi.

It is an object of the present invention to provide compounds with animproved activity.

We have found that this object is achieved by the phenylcarbamates Idefined at the outset. We have furthermore found processes andintermediates for their preparation and compositions comprising them forcontrolling animal pests and harmful fungi, and their use for thispurpose.

The compounds I are accessible via a variety of routes by methods knownper se from the literature.

In principle, it is irrelevant when synthesizing the compounds I whetherthe group --N(OR²)--COXR¹ or the group --CH₂ OCR³ ═NN═CR⁴ R⁵ isconstructed first.

The way in which the --CH₂ OCR³ ═NN═CR⁴ R⁵ side chain is synthesizeddepends essentially on the type of the substituent R³. For reasons ofclarity, the group --N(OR²)--COXR¹, or a suitable precursor of thisgroup, is abbreviated to # in the equations which follow.

If # is --N(OR²)--COXR¹, β denotes compounds of the formula II and αdenotes compounds of the formula I.

If # is --NHOH, β denotes L¹ -substituted ortho-hydroxyaminotoluenewhich is substituted by R_(m), and α denotes compounds of the formula V.If # is --NO₂, β denotes L¹ -substituted ortho-nitrotoluene which issubstituted by R_(m) and α denotes compounds IV.

1.1 In the event that R³ is not halogen, a procedure is generallyfollowed when constructing the --CH₂ OCR³ ═NN═CR⁴ R⁵ side chain in whicha benzyl derivative of the formula β is reacted with a carbohydrazide ofthe formula III. ##STR3##

L¹ in formula β, is a nucleophilically exchangeable leaving group, eg.halogen or sulfonate groups, preferably chlorine, bromine, iodine,mesylate, tosylate or triflate.

This reaction is usually carried out at from -10° C. to 80° C.,preferably 0° C. to 50° C., in an inert organic solvent in the presenceof a base [cf. Houben-Weyl, Vol. E 14b, p. 370 et seq. and Houben-Weyl,Vol. 10/1, p. 1189 et seq.].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, alcohols such as methanol, ethanol,n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethylsulfoxide, dimethylformamide and water, especially preferablydimethylformamide, acetonitrile, toluene, tert-butyl methyl ether andwater. Mixtures of these can also be used.

Suitable bases are, generally, inorganic compounds such as alkali metalhydroxides and alkaline earth metal hydroxides such as lithiumhydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide,alkali metal oxides and alkaline earth metal oxides such as lithiumoxide, sodium oxide, calcium oxide and magnesium oxide, alkali metalhydrides and alkaline earth metal hydrides such as lithium hydride,sodium hydride, potassium hydride and calcium hydride, alkali metalamides such as lithium amide, sodium amide and potassium amide, alkalimetal carbonates and alkaline earth metal carbonates such as lithiumcarbonate and calcium carbonate, and also alkali metal hydrogencarbonates such as sodium hydrogen carbonate, organometal compounds, inparticular alkali metal alkyls such as methyllithium, butyllithium andphenyllithium, alkylmagnesium halides such as methylmagnesium chloride,and alkali metal alkoxides and alkaline earth metal alkoxides such assodium methoxide, sodium ethoxide, potassium ethoxide, potassiumtert-butoxide and dimethoxymagnesium, furthermore organic bases, eg.tertiary amines such as trimethylamine, triethylamine,tri-isopropylamine and N-methylpiperidine, pyridine, substitutedpyridines such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Sodium hydride, potassium hydroxide, potassiumcarbonate and triethylamine are especially preferred.

In general, the bases are employed in catalytic amounts, but they canalso be used in equimolar amounts, in an excess or, if desired, as thesolvent.

The starting materials are generally reacted with each other inequimolar amounts. It may be advantageous for the yield to employ III inan excess based on β.

Those starting substances of the formula II required for the preparationof compounds I which have not already been described in the literaturecited at the outset can be prepared by the methods described therein.

Equally, those starting substances of the formula III which are notalready known from the literature [cf. Tetrahedron 1987, 4185;Houben-Weyl, Register der Stoffklassen [Register of Substance Classes]Part A, Vol. 16/2, p. 439 et seq.] can be prepared by the known methods.

1.2 Compounds α where R³ is a halogen atom are obtained by processesknown per se from the corresponding precursors where the radical inquestion is a hydroxyl group [cf. Houben-Weyl, Vol. E 5, p. 631 et seq.;J. Org. Chem. 36, (1971) 233; J. Org. Chem. 57, (1992) 3245].

1.3 Compounds α where R³ is bonded to the molecule skeleton via an O, Sor N atom are obtained by processes known per se from the correspondingprecursors where the radical in question is a halogen atom [cf.Houben-Weyl, Vol. E 5, p. 826 et seq.; J. Org. Chem. 36, (1971) 233; J.Org. Chem. 46, (1981) 3623].

1.4 Compounds α where R³ is bonded to the molecule via an oxygen atomare also obtained by processes known per se by means of etherifying thecorresponding precursors where the radical in question is a hydroxylgroup [cf. Houben-Weyl, Vol. E 5, p. 826 et seq.; Aust. J. Chem. 27,(1974) 1341].

The construction of the group --N(OR²)--COXR¹ is known, for example,from the literature cited at the outset. For reasons of clarity, the CH₂OCR³ ═NN═CR⁴ R⁵ side chain, or a suitable precursor of this group, isabbreviated to * in the equations which follow.

If * is CH₂ OR³ ═N--N═CR⁴ R⁵, δ denotes compounds of the formula IV, εdenotes compounds of the formula V and η denotes compounds of theformula I.

If * is CH₂ L¹, δ denotes L¹ -substituted ortho-nitrotoluene which issubstitituted by R_(m), ε denotes L¹ -substitutedortho-hydroxyaminotoluene which is substituted by R_(m) and η denotes L¹-substituted N-acyl(hydroxyamino)toluene which is substituted by R_(m).

If * is CH₃, δ denotes an ortho-nitrotoluene which is substituted byR_(m), ε denotes an ortho-hydroxyaminotoluene which is substituted byR_(m) and η denotes an N-acyl(hydroxyamino)toluene which is substitutedby R_(m).

2.1 Compounds η where R² is hydrogen (IA) are generally obtained byreducing a nitrobenzene of the formula δ to give the correspondinghydroxylamine ε and then reacting ε to give η (where R² ═H) by means ofreaction with an acylating agent of formula VI. ##STR4##

L² in formula VI is, for example, halogen or aryloxy, in particularchlorine and phenoxy.

a) The reduction of δ to the hydroxylamine e is usually carried out atfrom -30° C. to 80° C., preferably 0° C. to 60° C., in an inert organicsolvent in the presence of a catalyst [cf. DE Application No. 19 50 2700.0].

b) The reaction of the hydroxylamine ε with VI is usually carried out atfrom -20° C. to 60° C., preferably 0° C. to 30° C., in an inert organicsolvent in the presence of a base [cf. WO-A 93/15046].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, alcohols such as methanol, ethanol,n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethylsulfoxide, dimethylformamide and water, especially preferablycyclohexane, toluene, methylene chloride, tert-butyl methyl ether andwater. Mixtures of these can also be used.

Suitable bases are, generally, inorganic compounds such as alkali metalhydroxides and alkaline earth metal hydroxides such as lithiumhydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide,alkali metal oxides and alkaline earth metal oxides such as lithiumoxide, sodium oxide, calcium oxide and magnesium oxide, alkali metalhydrides and alkaline earth metal hydrides such as lithium hydride,sodium hydride, potassium hydride and calcium hydride, alkali metalamides such as lithium amide, sodium amide and potassium amide, alkalimetal carbonates and alkaline earth metal carbonates such as lithiumcarbonate and calcium carbonate, and also alkali metal hydrogencarbonates such as sodium hydrogen carbonate, organometal compounds, inparticular alkali metal alkyls such as methyllithium, butyllithium andphenyllithium, alkylmagnesium halides such as methylmagnesium chloride,and alkali metal alkoxides and alkaline earth metal alkoxides such assodium methoxide, sodium ethoxide, potassium ethoxide, potassiumtert-butoxide and dimethoxymagnesium, furthermore organic bases, eg.tertiary amines such as trimethylamine, triethylamine,tri-isopropylamine and N-methylpiperidine, pyridine, substitutedpyridines such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Potassium carbonate, sodium hydroxide andtriethylamine are especially preferred.

In general, the bases are employed in catalytic amounts, but they canalso be used in equimolar amounts, in an excess or, if desired, as thesolvent.

The compounds η where R² is not hydrogen (IB) are obtained by reacting acompound of the formula η where R² ═H with a compound of the formula VIIin a manner known per se. ##STR5##

L³ in formula VII is, for example, halogen, mesylate, tosylate,carboxylate and sulfate, in particular chlorine, bromine, mesylate andR² --OSO₃ --.

This reaction is usually carried out at from -20° C. to 80° C.,preferably 0° C. to 60° C., in an inert organic solvent in the presenceof a base [cf. WO-A 93/15046].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene,o-, m- and p-xylene, halogenated hydrocarbons such as methylenechloride, chloroform and chlorobenzene, ethers such as diethyl ether,diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitriles such as acetonitrile and propionitrile,ketones such as acetone, methyl ethyl ketone, diethyl ketone andtert-butyl methyl ketone, alcohols such as methanol, ethanol,n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethylsulfoxide and dimethylformamide, especially preferably acetone, toluene,tert-butyl methyl ether, cyclohexane and water. Mixtures of these canalso be used.

Suitable bases are, generally, inorganic compounds such as alkali metalhydroxides and alkaline earth metal hydroxides such as lithiumhydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide,alkali metal oxides and alkaline earth metal oxides such as lithiumoxide, sodium oxide, calcium oxide and magnesium oxide, alkali metalhydrides and alkaline earth metal hydrides such as lithium hydride,sodium hydride, potassium hydride and calcium hydride, alkali metalamides such as lithium amide, sodium amide and potassium amide, alkalimetal carbonates and alkaline earth metal carbonates such as lithiumcarbonate and calcium carbonate, and also alkali metal hydrogencarbonates such as sodium hydrogen carbonate, organometal compounds, inparticular alkali metal alkyls such as methyllithium, butyllithium andphenyllithium, alkylmagnesium halides such as methylmagnesium chloride,and alkali metal alkoxides and alkaline earth metal alkoxides such assodium methoxide, sodium ethoxide, potassium ethoxide, potassiumtert-butoxide and dimethoxymagnesium, furthermore organic bases, eg.tertiary amines such as trimethylamine, triethylamine,tri-isopropylamine and N-methylpiperidine, pyridine, substitutedpyridines such as collidine, lutidine and 4-dimethylaminopyridine, andalso bicyclic amines. Potassium carbonate, sodium hydroxide andtriethylamine are especially preferred.

In general, the bases are employed in catalytic amounts, but they canalso be used in equimolar amounts, in an excess or, if desired, as thesolvent.

The reaction mixtures are worked up in the customary manner, eg. bymixing with water, phase separation and, if desired, chromatographicpurification of the crude products. Some of the intermediates and endproducts are obtained in the form of colorless or pale brown, viscousoils which are freed or purified from volatile components under reducedpressure at moderately elevated temperature. If the intermediates andend products are obtained as solids, they may also be purified byrecrystallization or digestion.

When the compounds I are prepared, they may be obtained, because oftheir C═N double bonds, in the form of E/Z isomer mixtures, which can beseparated into the individual compounds in the customary manner, eg. bycrystallization or chromatography.

If isomer mixtures result from the synthesis, however, a separation isgenerally not absolutely necessary since, in some cases, the individualisomers may be converted into each other during preparation for use orupon use (eg. when exposed to light, acids or bases). Such conversionsmay also take place after use, for example in the case of planttreatment in the treated plant or in the harmful fungus or animal pestto be controlled.

With a view to the --CR³ ═N--N═CR⁴ R⁵ double bonds, the cis isomers ofthe compounds I (configuration based on the radical R³ relative to the--N═CR⁴ R⁵ group, or based on the radical R⁴ relative to the --N═CR³group) are generally preferred regarding their activity.

The compounds I may contain acidic or basic centers and, accordingly,form acid addition products or base addition products or salts.

Acids for acid addition products are, inter alia, mineral acids (eg.hydrohalic acids such as hydrochloric and hydrobromic acid, phosphoricacid, sulfuric acid, nitric acid), organic acids (eg. formic acid,acetic acid, oxalic acid, malonic acid, lactic acid, malic acid,succinic acid, tartaric acid, citric acid, salicylic acid,p-toluenesulfonic acid, dodecylbenzenesulfonic acid) or otherproton-acidic compounds (eg. saccharin).

Bases for base addition products are, inter alia, oxides, hydroxides,carbonates or hydrogen carbonates of alkali metals or alkaline earthmetals (eg. potassium hydroxide, potassium carbonate, sodium hydroxideor sodium carbonate) or ammonium compounds (eg. ammonium hydroxide).

In the definitions of the compounds I given at the outset, collectiveterms were used which generally represent the following groups:

Halogen: fluorine, chlorine, bromine and iodine;

Alkyl: straight-chain or branched alkyl groups having 1 to 10 carbonatoms, eg. C₁ -C₆ -alkyl such as methyl, ethyl, propyl, 1-methylethyl,butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl,1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-l-methylpropyl and 1-ethyl-2-methylpropyl;

Alkylamino: an amino group which has attached to it a straight-chain orbranched alkyl group having 1 to 6 carbon atoms as mentioned above;

Dialkylamino: an amino group which has attached to it two straight-chainor branched alkyl groups which are independent of one another and whichhave in each case attached to them 1 to 6 carbon atoms as mentionedabove;

Alkylcarbonyl: straight-chain or branched alkyl groups having 1 to 10carbon atoms which are bonded to the skeleton via a carbonyl group(--CO--);

Alkylsulfonyl: straight-chain or branched alkyl groups having 1 to 10carbon atoms which are bonded to the skeleton via a sulfonyl group(--SO₂ --);

Alkylsulfoxyl: straight-chain or branched alkyl groups having 1 to 6carbon atoms which are bonded to the skeleton via a sulfoxyl group(--S(═O)--);

Alkylaminocarbonyl: alkylamino groups having 1 to 6 carbon atoms asmentioned above which are bonded to the skeleton via a carbonyl group(--CO--);

Dialkylaminocarbonyl: dialkylamino groups having in each case 1 to 6carbon atoms per alkyl radical as mentioned above which are bonded tothe skeleton via a carbonyl group (--CO--);

Alkylaminothiocarbonyl: alkylamino groups having 1 to 6 carbon atoms asmentioned above which are bonded to the skeleton via a thiocarbonylgroup (--CS--);

Dialkylaminothiocarbonyl: dialkylamino groups having in each case 1 to 6carbon atoms per alkyl radical as mentioned above which are bonded tothe skeleton via a thiocarbonyl group (--CS--);

Haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbonatoms, it being possible for some or all of the hydrogen atoms in thesegroups to be replaced by halogen atoms as mentioned above, eg. C₁ -C₂-haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl,fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

Alkoxy: straight-chain or branched alkyl groups having 1 to 6 carbonatoms as mentioned above which are bonded to the skeleton via an oxygenatom (--O--), eg. C₁ -C₆ -alkoxy such as methyloxy, ethyloxy, propyloxy,1-methylethyloxy, butyloxy, 1-methylpropyloxy, 2-methylpropyloxy,1,1-dimethylethyloxy, pentyloxy, 1-methylbutyloxy, 2-methylbutyloxy,3-methylbutyloxy, 2,2-dimethylpropyloxy, 1-ethylpropyloxy, hexyloxy,1,1-dimethylpropyloxy, 1,2-dimethylpropyloxy, 1-methylpentyloxy,2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy,1,1-dimethylbutyloxy, 1,2-dimethylbutyloxy, 1,3-dimethylbutyloxy,2,2-dimethylbutyloxy, 2,3-dimethylbutyloxy, 3,3-dimethylbutyloxy,1-ethylbutyloxy, 2-ethylbutyloxy, 1,1,2-trimethylpropyloxy,1,2,2-trimethylpropyloxy, 1-ethyl-1-methylpropyloxy and1-ethyl-2-methylpropyloxy;

Alkoxycarbonyl: straight-chain or branched alkyl groups having 1 to 6carbon atoms which are bonded to the skeleton via an oxycarbonyl group(--OC(═O)--);

Haloalkoxy: straight-chain or branched alkyl groups having 1 to 6 carbonatoms, it being possible for some or all of the hydrogen atoms in thesegroups to be replaced by halogen atoms as mentioned above, and thesegroups being bonded to the skeleton via an oxygen atom;

Alkylthio: straight-chain or branched alkyl groups having 1 to 6 carbonatoms as mentioned above which are bonded to the skeleton via a sulfuratom (--S--), eg. C₁ -C₆ -alkylthio such as methylthio, ethylthio,propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio,2-methylpropylthio, 1,1-dimethylethylthio, pentylthio,1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,2,2-dimethylpropylthio, l-ethylpropylthio, hexylthio,1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio,2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio,1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio,1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and1-ethyl-2-methylpropylthio;

Cycloalkyl: monocyclic alkyl groups having 3 to 6 carbon ring members,eg. cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

Alkenyl: straight-chain or branched alkenyl groups having 2 to 10 carbonatoms and one double bond in any position, eg. C₂ -C₆ -alkenyl such asethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl,3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

Alkenyloxy: straight-chain or branched alkenyl groups having 2 to 6carbon atoms and one double bond in any position which are bonded to theskeleton via an oxygen atom (--O--);

Alkenylthio and alkenylamino: straight-chain or branched alkenyl groupshaving 2 to 6 carbon atoms and one double bond in any position which arebonded to the skeleton via a sulfur atom (alkenylthio) or a nitrogenatom (alkenylamino);

Alkenylcarbonyl: straight-chain or branched alkenyl groups having 2 to10 carbon atoms and one double bond in any position which are bonded tothe skeleton via a carbonyl group (--CO--);

Alkynyl: straight-chain or branched alkynyl groups having 3 to 10 carbonatoms and one triple bond in any position, eg. C₃ -C₆ -alkynyl such as2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl,3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl,1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl,2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl,1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl,2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;

Alkynyloxy, alkynylthio and alkynylamino: straight-chain or branchedalkynyl groups having 2 to 6 carbon atoms and one triple bond in anyposition which are bonded to the skeleton via an oxygen atom(alkynyloxy), via a sulfur atom (alkynylthio) or via a nitrogen atom(alkynylamino);

Alkynylcarbonyl: straight-chain or branched alkynyl groups having 3 to10 carbon atoms and one triple bond in any position which are bonded tothe skeleton via a carbonyl group (--CO--);

Cycloalkenyl, cycloalkenyloxy, cycloalkenylthio and cycloalkenylamino:monocyclic alkenyl groups having 3 to 6 carbon ring members which arebonded to the skeleton directly or via an oxygen atom (cycloalkenyloxy),via a sulfur atom (cycloalkenylthio) or via a nitrogen atom(cycloalkenylamino), eg. cyclobutenyl, cyclopentenyl or cyclohexenyl;

Cycloalkoxy, cycloalkylthio and cycloalkylamino: monocyclic alkyl groupshaving 3 to 6 carbon ring members which are bonded to the skeleton viaan oxygen atom (cycloalkyloxy), via a sulfur atom (cycloalkylthio) orvia a nitrogen atom (cycloalkylamino), eg. cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl;

Heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyclylamino:three- to six-membered, saturated or partially unsaturated mono- orpolycyclic heterocycles which contain one to three hetero atoms selectedfrom a group consisting of oxygen, nitrogen and sulfur and which arebonded to the skeleton directly or via an oxygen atom (heterocyclyloxy),via a sulfur atom (heterocyclylthio) or via a nitrogen atom(heterocyclylamino), eg. 2-tetrahydrofuranyl, oxiranyl,3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl,2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl,4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,5-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,2,4-triazolidin-5-yl,1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl,1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl,2,3-dihydrofur-4-yl, 2,3-dihydrofur-5-yl, 2,5-dihydrofur-2-yl,2,5-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl,2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl,2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl,2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl,2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl,2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl,4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl,4,5-dihydroisoxazol-5-yl, 2,3-dihydroisothiazol-3-yl,2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl,4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl,4,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-3-yl,2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl,4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl,2,5-dihydropyrazol-3-yl, 2,5-dihydropyrazol-4-yl,2,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl,2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl,4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl,2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl,2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl,4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl,4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl,2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl,2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl,2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl,4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl,2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl,2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl,3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl,4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl,4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl,1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl,1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl,1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl,4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl,2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl,1,3-dihydrooxazin-2-yl;

Aryl, aryloxy, arylthio, arylcarbonyl and arylsulfonyl: aromatic mono-or polycyclic hydrocarbon radicals which are bonded to the skeletondirectly or via an oxygen atom (--O--; aryloxy), via a sulfur atom(--S--; arylthio), via a carbonyl group (--CO--; arylcarbonyl) or via asulfonyl group (--SO₂ --; arylsulfonyl), eg. phenyl, naphthyl andphenanthrenyl, or phenyloxy, naphthyloxy and phenanthrenyloxy and thecorresponding carbonyl and sulfonyl radicals;

Arylamino: aromatic mono- or polycyclic hydrocarbon radicals which arebonded to the skeleton via a nitrogen atom;

Hetaryl, hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl:aromatic mono- or polycyclic radicals which, besides carbon ringmembers, can additionally contain one to four nitrogen atoms, or one tothree nitrogen atoms and one oxygen or one sulfur atom, or one oxygen orone sulfur atom, and which are bonded to the skeleton directly or via anoxygen atom (--O--; hetaryloxy), via a sulfur atom (--S--; hetarylthio),via a carbonyl group (--CO--; hetarylcarbonyl) or via a sulfonyl group(--SO₂ --; hetarylsulfonyl), eg.

5-membered hetaryl containing one to three nitrogen atoms: 5-memberedhetaryl ring groups which, besides carbon atoms, can contain one tothree nitrogen atoms as ring members, eg. 2-pyrrolyl, 3-pyrrolyl,3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl,5-imidazolyl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl,1,2,3-triazol-4-yl, 1,2,3-triazol-5-yl, 1,3,4-triazol-2-yl and1,3,4-triazol-5-yl;

5-membered hetaryl containing one to four nitrogen atoms or one to threenitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfuratom: 5-membered hetaryl ring groups which, besides carbon atoms, cancontain one to four nitrogen atoms or one to three nitrogen atoms andone sulfur or oxygen atom, or one oxygen or sulfur atom as ring members,eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl,3-isoxazolyl, ⁴ -isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl,1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl,1,3,4-oxadiazol-2-yl, 1,3,4-oxadiazol-5-yl, 1,3,4-thiadiazol-2-yl,1,3,4-thiadiazol-5-yl, 1,3,4-triazol-2-yl and 1,3,4-triazol-5-yl;

benzo-fused 5-membered hetaryl containing one to three nitrogen atoms orone nitrogen atom and/or one oxygen or sulfur atom: 5-membered hetarylring groups which, besides carbon atoms, can contain one to fournitrogen atoms, or one to three nitrogen atoms and one sulfur or oxygenatom or one oxygen or one sulfur atom as ring members, and in which twoadjacent carbon ring members or one nitrogen and one adjacent carbonring member can be bridged by a buta-1,3-diene-1,4-diyl group;

5-membered hetaryl, bonded via nitrogen and containing one to fournitrogen atoms, or benzo-fused 5-membered hetaryl, bonded via nitrogenand containing one to three nitrogen atoms: 5-membered hetaryl ringgroups which, besides carbon atoms, can contain one to four nitrogenatoms, or one to three nitrogen atoms, respectively, as ring members andin which two adjacent carbon ring members or one nitrogen and oneadjacent carbon ring member can be bridged by a buta-1,3-diene-1,4-diylgroup, these rings being bonded to the skeleton via one of the nitrogenring members;

6-membered hetaryl containing one to three, or one to four, nitrogenatoms: 6-membered hetaryl ring groups which, besides carbon atoms, cancontain one to three, or one to four, nitrogen atoms, respectively, asring members, eg. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl,4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl,1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl;

benzo-fused 6-membered hetaryl containing one to four nitrogen atoms:6-membered hetaryl ring groups in which two adjacent carbon ring memberscan be bridged by a buta-1,3-diene-1,4-diyl group, eg. quinoline,isoquinoline, quinazoline and quinoxaline, and the corresponding oxy,thio, carbonyl or sulfonyl groups.

Hetarylamino: aromatic mono- or polycyclic radicals which, besidescarbon ring members, can additionally contain one to four nitrogen atomsor one to three nitrogen atoms and one oxygen or one sulfur atom andwhich are bonded to the skeleton via a nitrogen atom.

The term "partially or fully halogenated" is used to indicate that someor all of the hydrogen atoms in thus characterized groups can bereplaced by identical or different halogen atoms as mentioned above.

The term "substituted or unsubstituted" when referring to the radicalsmentioned in the definition of R² is used to indicate that the groups inquestion can be partially or fully halogenated and/or can have attachedto them one to three of the following groups:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl,

C₁ -C₆ -alkylcarbonyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylsulfoxyl, C₁-C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆-alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆ -alkylamino, C₁ -C₆-alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl, C₁ -C₆-alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₂ -C₆-alkenyl, C₂ -C₆ -alkenyloxy, C (═NOR^(b)) A_(n) --R^(c) or benzyloxyand benzylthio which are substituted by customary groups;

C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkoxy, heterocyclyl, heterocyclyloxy,benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio,it being possible for the cyclic groups, in turn, to be partially orfully halogenated or to have attached to them one to three of thefollowing groups: cyano, nitro, hydroxyl, mercapto, amino, carboxyl,aminocarbonyl, aminothiocarbonyl, halogen, C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylsulfoxyl, C₁ -C₆-alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio,C₁ -C₆ -alkylamino, di-C₁ -C₆ -alkylamino, C₁ -C₆ -alkylaminocarbonyl,di-C₁ -C₆ -alkylaminocarbonyl, C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆-alkylaminothiocarbonyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkenyloxy,C(═NOR^(b))--A_(n) --R^(c), or benzyl, benzyloxy, aryl, aryloxy,arylthio, hetaryl, hetaryloxy and hetarylthio which are substituted bycustomary groups.

The term "substituted by customary groups" is used to indicate that theradicals in question can be partially or fully halogenated and/or haveattached to them one to three of the following substituents: cyano,nitro, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -haloalkylthio, C₁ -C₄-alkylcarbonyl, C₁ -C₄ -alkoxycarbonyl, phenyl, phenoxy, benzyl andbenzyloxy, and/or can have attached to them a group C(═NOR^(b))--A_(n)--R^(c).

Compounds of the formula I which must be emphasized with a view to theirbiological activity are those where the substituents and the index havethe following meanings:

R is cyano, nitro, trifluoromethyl, halogen, C₁ -C₄ -alkyl or C₁ -C₄-alkoxy;

m is 0, 1 or 2, it being possible for the radicals R to be different ifn is 2;

R¹ is alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, and, in theevent that X is NR^(a), additionally hydrogen;

X is a direct bond, O or NR^(a) ;

R^(a) is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl;

R² is hydrogen,

unsubstituted or substituted alkyl, alkenyl, alkynyl, cycloalkyl,cycloalkenyl, cycloalkynyl, alkylcarbonyl or alkoxycarbonyl;

R³ and R⁴ independently of one another are

hydrogen, cyano, nitro, hydroxyl, amino, halogen,

C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino,di-C₁ -C₆ -alkylamino, C₂ -C₆ -alkenyl, C₂ -C₆ -alkenyloxy, C₂ -C₆-alkenylthio, C₂ -C₆ -alkenylamino, N--C₂ -C₆ -alkenyl-N--C₁ -C₆-alkylamino, C₂ -C₆ -alkynyl, C₂ -C₆ -alkynyloxy, C₂ -C₆ -alkynylthio,C₂ -C₆ -alkynylamino, N--C₂ -C₆ -alkynyl-N--C₁ -C₆ -alkylamino, it beingpossible for the hydrocarbon radicals of these groups to be partially orfully halogenated and/or to have attached to them one to three of thefollowing radicals:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl,

C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl, C₁ -C₆-alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylsulfoxyl, C₁ -C₆ -alkoxy, C₁ -C₆-haloalkoxy, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆-alkylamino, di-C₁ -C₆ -alkylamino, C₂ -C₆ -alkenyloxy,

C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyloxy, heterocyclyl,heterocyclyloxy, aryl, aryloxy, aryl-C₁ -C₄ -alkoxy, arylthio, aryl-C₁-C₄ -alkylthio, hetaryl, hetaryloxy, hetaryl-C₁ -C₄ -alkoxy, hetarylthioand hetaryl-C₁ -C₄ -alkylthio, it being possible for the cyclicradicals, in turn, to be partially or fully halogenated and/or to haveattached to them one to three of the following groups: cyano, nitro,hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl,C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylsulfoxyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy,C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆-alkylamino, C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl,C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₂-C₆ -alkenyl, C₂ -C₆ -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy,arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR^(b))--A_(n)--R^(c) ; C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyloxy, C₃ -C₆-cycloalkylthio, C₃ -C₆ -cycloalkylamino, N--C₃ -C₆ -cycloalkyl-N--C₁-C₆ -alkylamino, C₅ -C₈ -cycloalkenyl, C₅ -C₈ -cycloalkenyloxy, C₅ -C₈-cycloalkenylthio, C₅ -C₈ -cycloalkenylamino, N--C₅ -C₈-cycloalkenyl-N--C₁ -C₆ -alkylamino, heterocyclyl, heterocyclyloxy,heterocyclylthio, heterocyclylamino, N-heterocyclyl-N--C₁ -C₆-alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N--C₁ -C₆-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino,N-hetaryl-N--C₁ -C₆ -alkylamino, it being possible for the cyclicradicals to be partially or fully halogenated and/or to have attached tothem one to three of the following groups:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl,

C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylsulfoxyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy,C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆-alkylamino, C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl,C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₂-C₆ -alkenyl, C₂ -C₆ -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy,hetaryl, hetaryloxy, C(═NOR^(b))--A_(n) --R^(c) or NR^(f) --CO--D--R^(g);

A is oxygen, sulfur or nitrogen, the nitrogen having attached to ithydrogen or C₁ -C₆ -alkyl;

D is a direct bond, oxygen or NR^(h) ;

n is 0 or 1;

R^(b) and R^(c) independently of one another are hydrogen or C₁ -C₆-alkyl;

R^(f) is hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆-alkynyl, C₁ -C₆ -alkoxy, C₂ -C₆ -alkenyloxy, C₂ -C₆ -alkynyloxy, C₁ -C₆-alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy and C₁ -C₆-alkoxycarbonyl;

R^(g), R^(h) independently of one another are hydrogen, C₁ -C₆ -alkyl,C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₃ -C₆-cycloalkenyl, aryl, aryl-C₁ -C₆ -alkyl, hetaryl and hetaryl-C₁ -C₆-alkyl;

R⁵ is one of the groups mentioned under R³, or a group CR^(d) ═NOR^(e) ;

R^(d) is one of the groups mentioned under R³ ;

R^(e) is hydrogen,

C₁ -C₁₀ -alkyl, C₃ -C₆ -cycloalkyl, C₂ -C₁₀ -alkenyl, C₂ -C₁₀ -alkynyl,C₁ -C₁₀ -alkylcarbonyl, C₂ -C₁₀ -alkenylcarbonyl, C₂ -C₁₀-alkynylcarbonyl or C₁ -C₁₀ -alkylsulfonyl, it being possible for theseradicals to be partially or fully halogenated and/or to have attached tothem one to three of the following groups:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl,

C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylsulfoxyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆-alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆-alkylamino, C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl,C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₂-C₆ -alkenyl, C₂ -C₆ -alkenyloxy, C₃ -C₆ -cycloalkyl, C₃ -C₆-cycloalkyloxy, heterocyclyl, heterocyclyloxy, benzyl, benzyloxy, aryl,aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, it beingpossible for the last twelve groups mentioned, in turn, to be partiallyor fully halogenated and/or to have attached to them one to three of thefollowing groups:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl,

C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylsulfoxyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy,C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆-alkylamino, C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl,C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₂-C₆ -alkenyl, C₂ -C₆ -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy,arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR^(b))--A_(n) --R^(c);

aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl orhetarylsulfonyl, it being possible for these radicals to be partially orfully halogenated and/or to have attached to them one to three of thefollowing groups:

cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl,

C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylcarbonyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylsulfoxyl, C₃ -C₆ -cycloalkyl, C₁ -C₆-alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio,C₁ -C₆ -alkylamino, di-C₁ -C₆ -alkylamino, C₁ -C₆ -alkylaminocarbonyl,di-C₁ -C₆ -alkylaminocarbonyl, C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆-alkylaminothiocarbonyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkenyloxy, benzyl,benzyloxy, aryl, aryloxy, hetaryl, hetaryloxy or C(═NOR^(b))--A_(n)--R^(c),

and the salts thereof.

Preferred compounds of the formula I with regard to their biologicalaction are those where m is 0 or 1, in particular 0.

In the event that m is not 0, preferred compounds I are those where R isfluorine, chlorine, methyl and trifluoromethyl.

Particularly preferred compounds I are those where X is oxygen.

Furthermore, especially preferred compounds I are those where X is NH.

Equally, especially preferred compounds I are those where X is a directlinkage.

Particularly preferred compounds I are those where R¹ is methyl.

Furthermore, especially preferred compounds I are those where R¹ isethyl.

Equally, especially preferred compounds I are those where R¹ iscyclopropyl.

Besides, especially preferred compounds I are those where R¹ is hydrogen(X is NR^(a)).

Particularly preferred compounds I are those where R² is hydrogen.

Furthermore, especially preferred compounds I are those where R² ismethyl.

Equally, especially preferred compounds I are those where R² is ethyl.

Besides, especially preferred compounds I are those where R² ismethoxymethyl, allyl or propargyl.

Particularly preferred compounds I are those where R³ is C₁ -C₄ -alkyl,especially methyl.

Furthermore, especially preferred compounds I are those where R³ isaryl, especially substituted or unsubstituted phenyl.

Equally, especially preferred compounds I are those where R³ is hetaryl,especially substituted or unsubstituted isoxazolyl, pyrazolyl andpyridinyl.

Besides, especially preferred compounds I are those where R³ issubstituted or unsubstituted cycloalkyl, especially cycloalkyl.

Particularly preferred compounds I are those where R⁴ is C₁ -C₄ -alkyl,especially methyl.

Furthermore, especially preferred compounds I are those where R⁴ isaryl, especially substituted or unsubstituted phenyl.

Equally, especially preferred compounds I are those where R⁴ issubstituted or unsubstituted cycloalkyl, especially cycloalkyl.

Besides, especially preferred compounds I are those where R⁴ is hetaryl,especially substituted or unsubstituted isoxazolyl, pyrazolyl andpyridinyl.

Particularly preferred compounds I are those where R⁵ is C₁ -C₄ -alkyl.

Furthermore, especially preferred compounds I are those where R⁵ isaryl, especially substituted or unsubstituted phenyl.

Equally, especially preferred compounds I are those where R⁵ is hetaryl,especially substituted or unsubstituted isoxazolyl, pyrazolyl andpyridinyl.

Besides, especially preferred compounds I are those where R⁵ is a groupCR^(d) ═NOR^(e).

In the event that R⁵ is a group CR^(d) ═NOR^(e), preferred compounds Iare those where R^(d) is C₁ -C₄ -alkyl, especially methyl.

Particularly preferred compounds I are those where R^(d) is aryl,especially substituted or unsubstituted phenyl.

Furthermore, especially preferred compounds I are those where R^(d) ishetaryl, especially substituted or unsubstituted isoxazolyl, pyrazolyland pyridinyl.

Equally, especially preferred compounds I are those where R^(d) issubstituted or unsubstituted cycloalkyl, especially cycloalkyl.

Besides, especially preferred compounds I are those where R^(e) is C₁-C₄ -alkyl, especially methyl.

Furthermore, especially preferred compounds I are those where R^(e) issubstitute d or unsubstituted alkenyl, especially allyl.

Equally, especially preferred compounds I are those where R^(e) issubstituted or unsubstituted alkynyl, especially propargyl.

Besides, especially preferred compounds I are those where R^(e) ismethoxyethyl.

Particularly preferred compounds I with regard to their use are thosecompiled in the tables which follow. Furthermore, the groups mentionedin the tables for a substituent are, on their own and independently ofthe combination in which they are mentioned, an especially preferredembodiment of the substituent in question.

Table 1

Compounds of the general formula IA (m=0) where XR¹ is methyl, R³ ismethyl and the combination of the substituents R⁴ and R⁵ corresponds ineach case to one line of Table A ##STR6##

Table 2

Compounds of the general formula IA (m=0) where XR¹ is ethyl, R³ ismethyl and the combination of the substituents R⁴ and R⁵ corresponds ineach case to one line of Table A.

Table 3

Compounds of the general formula IA (m=0) where XR1 is methoxy, R³ ismethyl and the combination of the substituents R⁴ and R⁵ corresponds ineach case to one line of Table A.

Table 4

Compounds of the general formula IA (m=0) where XR¹ is ethoxy, R³ ismethyl and the combination of the substituents R⁴ and R⁵ corresponds ineach case to one line of Table A.

Table 5

Compounds of the general formula IA (m=0) where XR¹ is methylamino, R³is methyl and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 6

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² ismethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A. ##STR7##

Table 7

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² ismethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 8

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 9

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² ismethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 10

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 11

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² isethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 12

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² isethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 13

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² isethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 14

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² isethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 15

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is ethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 16

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 17

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 18

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethoxy, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 19

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethoxy, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 20

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethylamino, R³ is methyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 21

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is methyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 22

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is methyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 23

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is methyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 24

Compounds of the general formula IB where R_(m) is 3-chlorine; XR¹ isethoxy, R² is methyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 25

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethylamino, R² is methyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 26

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is ethyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 27

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is ethyl, R³ is methyl and the combination of the substituentsR⁴ and R⁵ corresponds in each case to one line of Table A.

Table 28

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is ethyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 29

Compounds of the general formula IB where R_(m) is 3-chlorine XR¹ isethoxy, R² is ethyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 30

Compounds of the general formula IB where R_(m) is 3-chlorine XR¹ ismethylamino, R² is ethyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 31

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 32

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethyl, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 33

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethoxy, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 34

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethoxy, R³ is methyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 35

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethylamino, R³ is methyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 36

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethyl, R² is methyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 37

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is methyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 38

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is methyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 39

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is methyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 40

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is methyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 41

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethyl, R² is ethyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 42

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is ethyl, R³ is methyl and the combination of the substituentsR⁴ and R⁵ corresponds in each case to one line of Table A.

Table 43

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is ethyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 44

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is ethyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 45

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is ethyl, R³ is methyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 46

Compounds of the general formula IA (m=0) where XR¹ is methyl, R³ ismethoxy and the combination of the substituents R⁴ and R⁵ corresponds ineach case to one line of Table A.

Table 47

Compounds of the general formula IA (m=0) where XR¹ is ethyl, R³ ismethoxy and the combination of the substituents R⁴ and R⁵ corresponds ineach case to one line of Table A.

Table 48

Compounds of the general formula IA (m=0) where XR¹ is methoxy, R³ ismethoxy and the combination of the substituents R⁴ and R⁵ corresponds ineach case to one line of Table A.

Table 49

Compounds of the general formula IA (m=0) where XR¹ is ethoxy, R³ ismethoxy and the combination of the substituents R⁴ and R⁵ corresponds ineach case to one line of Table A.

Table 50

Compounds of the general formula IA (m=0) where XR¹ is methylamino, R³is methoxy and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 51

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² ismethyl, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 52

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² ismethyl, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 53

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 54

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² ismethyl, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 55

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is methyl, R³ is methoxy and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 56

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² isethyl, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 57

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² isethyl, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 58

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² isethyl, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 59

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² isethyl, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 60

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is ethyl, R³ is methoxy and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 61

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethyl, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 62

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethyl, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 63

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethoxy, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 64

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethoxy, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 65

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethylamino, R³ is methoxy and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 66

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is methyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 67

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is methyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 68

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is methyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 69

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethoxy, R² is methyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 70

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethylamino, R² is methyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 71

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is ethyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 72

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is ethyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 73

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is ethyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 74

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethoxy, R² is ethyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 75

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethylamino, R² is ethyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 76

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethyl, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 77

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethyl, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 78

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethoxy, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 79

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethoxy, R³ is methoxy and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 80

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethylamino, R³ is methoxy and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 81

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethyl, R² is methyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 82

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is methyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 83

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is methyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 84

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is methyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 85

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is methyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 86

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethyl, R² is ethyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 87

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is ethyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 88

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is ethyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 89

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is ethyl, R³ is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 90

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethylamino, R² is ethyl, R3 is methoxy and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 91

Compounds of the general formula IA (m=0) where XR¹ is methyl, R³ ishydroxyl and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 92

Compounds of the general formula IA (m=0) where XR¹ is ethyl, R³ ishydroxyl and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 93

Compounds of the general formula IA (m=0) where XR¹ is methoxy, R³ ishydroxyl and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 94

Compounds of the general formula IA (m=0) where XR¹ is ethoxy, R³ ishydroxyl and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 95

Compounds of the general formula IA (m=0) where XR¹ is methylamino, R³is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 96

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² ismethyl, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 97

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² ismethyl, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 98

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² ismethyl, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 99

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² ismethyl, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 100

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is methyl, R³ is hydroxyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 101

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² isethyl, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 102

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² isethyl, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 103

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² isethyl, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 104

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² isethyl, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 105

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is ethyl, R³ is hydroxyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 106

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethyl, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 107

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethyl, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 108

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethoxy, R³ is hydroxyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 109

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethoxy, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 110

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethylamino, R³ is hydroxyl and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 111

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is methyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 112

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is methyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 113

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is methyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 114

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethoxy, R² is methyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 115

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethylamino, R² is methyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 116

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is ethyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 117

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is ethyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 118

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is ethyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 119

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethoxy, R² is ethyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 120

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethylamino, R² is ethyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 121

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethyl, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 122

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethyl, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 123

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethoxy, R³ is hydroxyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 124

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethoxy, R³ is hydroxyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 125

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethylamino, R³ is hydroxyl and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 126

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethyl, R² is methyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 127

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is methyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 128

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is methyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 129

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is methyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 130

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is methyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 131

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethyl, R² is ethyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 132

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is ethyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 133

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is ethyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 134

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is ethyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 135

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is ethyl, R³ is hydroxyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 136

Compounds of the general formula IA (m=0) where XR¹ is methyl, R³ ishydrogen and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 137

Compounds of the general formula IA (m=0) where XR¹ is ethyl, R³ ishydrogen and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 138

Compounds of the general formula IA (m=0) where XR¹ is methoxy, R³ ishydrogen and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 139

Compounds of the general formula IA (m=0) where XR¹ is ethoxy, R³ ishydrogen and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 140

Compounds of the general formula IA (m=0) where XR¹ is methylamino, R³is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 141

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² ismethyl, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 142

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² ismethyl, R³ is hydrogen and the combination of the substituents R⁴ and R5corresponds in each case to one line of Table A.

Table 143

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² ismethyl, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 144

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² ismethyl, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 145

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is methyl, R³ is hydrogen and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 146

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² isethyl, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 147

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² isethyl, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 148

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² isethyl, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 149

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² isethyl, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 150

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is ethyl, R³ is hydrogen and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 151

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethyl, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 152

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethyl, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 153

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethoxy, R³ is hydrogen and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 154

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethoxy, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 155

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethylamino, R³ is hydrogen and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 156

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is methyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 157

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is methyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 158

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is methyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 159

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethoxy, R² is methyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 160

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethylamino, R² is methyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 161

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is ethyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 162

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is ethyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 163

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is ethyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 164

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethoxy, R² is ethyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 165

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethylamino, R² is ethyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 166

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethyl, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 167

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethyl, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 168

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethoxy, R³ is hydrogen and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 169

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethoxy, R³ is hydrogen and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 170

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethylamino, R³ is hydrogen and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 171

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethyl, R² is methyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 172

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is methyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 173

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is methyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 174

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is methyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 175

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is methyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 176

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is ethyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 177

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is ethyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 178

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is ethyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 179

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is ethyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 180

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is ethyl, R³ is hydrogen and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 181

Compounds of the general formula IA (m=0) where XR¹ is methyl, R³ ischlorine and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 182

Compounds of the general formula IA (m=0) where XR¹ is ethyl, R³ ischlorine and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 183

Compounds of the general formula IA (m=0) where XR¹ is methoxy, R³ ischlorine and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 184

Compounds of the general formula IA (m=0) where XR¹ is ethoxy, R³ ischlorine and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 185

Compounds of the general formula IA (m=0) where XR¹ is methylamino, R³is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 186

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² ismethyl, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 187

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² ismethyl, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 188

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² ismethyl, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 189

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² ismethyl, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 190

Compounds of the general formula IB (m=0) where XR1 is methylamino, R²is methyl, R³ is chlorine and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 191

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² isethyl, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 192

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² isethyl, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 193

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² isethyl, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 194

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² isethyl, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 195

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is ethyl, R³ is chlorine and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 196

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethyl, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 197

Compounds of the general formula IA where R_(m) is 3-chlorine, XR1 isethyl, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 198

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethoxy, R³ is chlorine and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 199

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethoxy, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 200

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethylamino, R³ is chlorine and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 201

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is methyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 202

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is methyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 203

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is methyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 204

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethoxy, R² is methyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 205

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethylamino, R² is methyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 206

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is ethyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 207

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is ethyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 208

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is ethyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 209

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethoxy, R² is ethyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 210

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethylamino, R² is ethyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 211

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethyl, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 212

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethyl, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 213

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethoxy, R³ is chlorine and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 214

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethoxy, R³ is chlorine and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 215

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethylamino, R³ is chlorine and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 216

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethyl, R² is methyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 217

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is methyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 218

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is methyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 219

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is methyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 220

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is methyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 221

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethyl, R² is ethyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 222

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is ethyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 223

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is ethyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 224

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is ethyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 225

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is ethyl, R³ is chlorine and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 226

Compounds of the general formula IA (m=0) where XR¹ is methyl, R³ ismethylthio and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 227

Compounds of the general formula IA (m=0) where XR¹ is ethyl, R³ ismethylthio and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 228

Compounds of the general formula IA (m=0) where XR¹ is methoxy, R³ ismethylthio and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 229

Compounds of the general formula IA (m=0) where XR¹ is ethoxy, R³ ismethylthio and the combination of the substituents R⁴ and R⁵ correspondsin each case to one line of Table A.

Table 230

Compounds of the general formula IA (m=0) where XR¹ is methylamino, R³is methylthio and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 231

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² ismethyl, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 232

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² ismethyl, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 233

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 234

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² ismethyl, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 235

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is methyl, R³ is methylthio and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 236

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² isethyl, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 237

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² isethyl, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 238

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² isethyl, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 239

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² isethyl, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 240

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is ethyl, R³ is methylthio and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 241

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethyl, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 242

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethyl, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 243

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethoxy, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 244

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethoxy, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 245

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethylamino, R³ is methylthio and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 246

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is methyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 247

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is methyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 248

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is methyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 249

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethoxy, R² is methyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 250

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethylamino, R² is methyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 251

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is ethyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 252

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is ethyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 253

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is ethyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 254

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethoxy, R² is ethyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 255

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethylamino, R² is ethyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 256

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethyl, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 257

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethyl, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 258

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethoxy, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 259

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethoxy, R³ is methylthio and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 260

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethylamino, R³ is methylthio and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 261

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is methyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 262

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is methyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 263

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is methyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 264

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is methyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 265

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is methyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 266

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethyl, R² is ethyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 267

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is ethyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 268

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is ethyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 269

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is ethyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 270

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is ethyl, R³ is methylthio and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 271

Compounds of the general formula IA (m=0) where XR¹ is methyl, R³ iscyclopropyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 272

Compounds of the general formula IA (m=0) where XR¹ is ethyl, R³ iscyclopropyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 273

Compounds of the general formula IA (m=0) where XR¹ is methoxy, R³ iscyclopropyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 274

Compounds of the general formula IA (m=0) where XR¹ is ethoxy, R³ iscyclopropyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 275

Compounds of the general formula IA (m=0) where XR¹ is methylamino, R³is cyclopropyl and the combination of the substituents R⁴ and R⁵corresponds in each case to one line of Table A.

Table 276

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² ismethyl, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 277

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² ismethyl, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 278

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² ismethyl, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 279

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² ismethyl, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 280

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is methyl, R³ is cyclopropyl and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 281

Compounds of the general formula IB (m=0) where XR¹ is methyl, R² isethyl, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 282

Compounds of the general formula IB (m=0) where XR¹ is ethyl, R² isethyl, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 283

Compounds of the general formula IB (m=0) where XR¹ is methoxy, R² isethyl, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 284

Compounds of the general formula IB (m=0) where XR¹ is ethoxy, R² isethyl, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 285

Compounds of the general formula IB (m=0) where XR¹ is methylamino, R²is ethyl, R³ is cyclopropyl and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 286

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethyl, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 287

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethyl, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 288

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethoxy, R³ is cyclopropyl and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 289

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ isethoxy, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 290

Compounds of the general formula IA where R_(m) is 3-chlorine, XR¹ ismethylamino, R³ is cyclopropyl and the combination of the substituentsR⁴ and R⁵ corresponds in each case to one line of Table A.

Table 291

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is methyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 292

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is methyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 293

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is methyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 294

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethoxy, R² is methyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 295

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethylamino, R² is methyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 296

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethyl, R² is ethyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 297

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethyl, R² is ethyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 298

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethoxy, R² is ethyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 299

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ isethoxy, R² is ethyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 300

Compounds of the general formula IB where R_(m) is 3-chlorine, XR¹ ismethylamino, R² is ethyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 301

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethyl, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 302

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethyl, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 303

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethoxy, R³ is cyclopropyl and the combination of the substituents R⁴and R⁵ corresponds in each case to one line of Table A.

Table 304

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ isethoxy, R³ is cyclopropyl and the combination of the substituents R⁴ andR⁵ corresponds in each case to one line of Table A.

Table 305

Compounds of the general formula IA where R_(m) is 6-methyl, XR¹ ismethylamino, R³ is cyclopropyl and the combination of the substituentsR⁴ and R⁵ corresponds in each case to one line of Table A.

Table 306

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethyl, R² is methyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 307

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is methyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 308

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is methyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 309

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is methyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 310

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is methyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 311

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethyl, R² is ethyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 312

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethyl, R² is ethyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 313

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethoxy, R² is ethyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 314

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ isethoxy, R² is ethyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 315

Compounds of the general formula IB where R_(m) is 6-methyl, XR¹ ismethylamino, R² is ethyl, R³ is cyclopropyl and the combination of thesubstituents R⁴ and R⁵ corresponds in each case to one line of Table A.

Table 316

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R^(d) is methyl, R^(e) is methyl and R⁴ is R^(x)-substituted phenyl, where Rx corresponds in each case to one line ofTable B. ##STR8##

Table 317

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R^(d) is methyl, R^(e) is methyl and R⁴ is R^(x)-substituted phenyl, where Rx corresponds in each case to one line ofTable B.

Table 318

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R^(d) is methyl, R^(e) is methyl and R⁴ isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 319

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R^(d) is methyl, R^(e) is methyl and R⁴ isR^(x) -substituted phenyl, where Rx corresponds in each case to one lineof Table B.

Table 320

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is ethyl, R^(d) is methyl, R^(e) is methyl and R⁴ is R^(x)-substituted phenyl, where Rx corresponds in each case to one line ofTable B.

Table 321

Compounds of the general formula IC (m=0) where XR1 is methoxy, R² isethyl, R³ is ethyl, R^(d) is methyl, R^(e) is methyl and R⁴ is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 322

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is ethyl, R^(d) is methyl, R^(e) is methyl and R⁴ isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 323

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is ethyl, R³ is ethyl, R^(d) is methyl, R^(e) is methyl and R⁴ is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 324

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is cyclopropyl, R^(d) is methyl, R^(e) is methyl and R⁴ isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 325

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² iscyclopropyl, R³ is cyclopropyl, R^(d) is methyl, R^(e) is methyl and R⁴is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 326

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is cyclopropyl, R^(d) is methyl, R^(e) is methyl and R⁴is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 327

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is cyclopropyl, R³ is cyclopropyl, R^(d) is methyl, R^(e) is methyl andR⁴ is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 328

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is methyl, R^(e) is methyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 329

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is methyl, R^(e) is methyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 330

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is methyl, R^(e) is methyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 331

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is methyl, R^(e) is methyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 332

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is ethyl, R^(e) is methyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 333

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is ethyl, R^(e) is methyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 334

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is ethyl, R^(e) is methyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 335

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is ethyl, R^(e) is methyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 336

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is iso-propyl, R^(e) is methyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 337

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is iso-propyl, R^(e) is methyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 338

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is iso-propyl, R^(e) is methyl and R^(d)is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 339

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is iso-propyl, R^(e) is methyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 340

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is methyl, R^(e) is ethyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 341

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is methyl, R^(e) is ethyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 342

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is methyl, R^(e) is ethyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 343

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is methyl, R^(e) is ethyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 344

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is methyl, R^(e) is n-propyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 345

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is methyl, R^(e) is n-propyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 346

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is methyl, R^(e) is n-propyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 347

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is methyl, R^(e) is n-propyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 348

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is methyl, R^(e) is iso-propyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 349

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is methyl, R^(e) is iso-propyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 350

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is methyl, R^(e) is iso-propyl and R^(d)is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 351

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is methyl, R^(e) is iso-propyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 352

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is methyl, R^(e) is tert-butyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 353

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is methyl, R^(e) is tert-butyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 354

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is methyl, R^(e) is tert-butyl and R^(d)is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 355

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is methyl, R^(e) is tert-butyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 356

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is methyl, R^(e) is benzyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 357

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is methyl, R^(e) is benzyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 358

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is methyl, R^(e) is benzyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 359

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is methyl, R^(e) is benzyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 360

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is methyl, R^(e) is propargyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 361

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is methyl, R^(e) is propargyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 362

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is methyl, R^(e) is propargyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 363

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is methyl, R^(e) is propargyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 364

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is methyl, R^(e) is bromopropargyl and R^(d)is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 365

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is methyl, R^(e) is bromopropargyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 366

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is methyl, R^(e) is bromopropargyl andR^(d) is R^(x) -substituted phenyl, where R^(x) corresponds in each caseto one line of Table B.

Table 367

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is methyl, R^(e) is bromopropargyl and R^(d)is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 368

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is methyl, R^(e) is iodopropargyl and R^(d)is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 369

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is methyl, R^(e) is iodopropargyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 370

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is methyl, R^(e) is iodopropargyl andR^(d) is R^(x) -substituted phenyl, where R^(x) corresponds in each caseto one line of Table B.

Table 371

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is methyl, R^(e) is iodopropargyl and R^(d)is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 372

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is methyl, R^(e) is allyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 373

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is methyl, R^(e) is allyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 374

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is methyl, R^(e) is allyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 375

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is methyl, R^(e) is allyl and R^(d) is R^(x)-substituted phenyl, where R^(x) corresponds in each case to one line ofTable B.

Table 376

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is methyl, R^(e) is trans-chloroallyl andR^(d) is R^(x) -substituted phenyl, where R^(x) corresponds in each caseto one line of Table B.

Table 377

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is methyl, R^(e) is trans-chloroallyl and R^(d)is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 378

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is methyl, R^(e) is transchloroallyl andR^(d) is R^(x) -substituted phenyl, where R^(x) corresponds in each caseto one line of Table B.

Table 379

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is methyl, R^(e) is trans-chloroallyl andR^(d) is R^(x) -substituted phenyl, where R^(x) corresponds in each caseto one line of Table B.

Table 380

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen, R³ is methyl, R⁴ is methyl, R^(e) is methoxyethyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 381

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl, R³ is methyl, R⁴ is methyl, R^(e) is methoxyethyl and R^(d) isR^(x) -substituted phenyl, where R^(x) corresponds in each case to oneline of Table B.

Table 382

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is hydrogen, R³ is methyl, R⁴ is methyl, R^(e) is methoxyethyl and R^(d)is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 383

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl, R³ is methyl, R⁴ is methyl, R^(e) is methoxyethyl and R^(d)is R^(x) -substituted phenyl, where R^(x) corresponds in each case toone line of Table B.

Table 384

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ishydrogen and the combination of the radicals R³, R⁴, R^(d) and R^(e)corresponds in each case to one line of Table C.

Table 385

Compounds of the general formula IC (m=0) where XR¹ is methoxy, R² ismethyl and the combination of the radicals R³, R⁴, R^(d) and R^(e)corresponds in each case to one line of Table C.

Table 386

Compounds of the general formula IC (m=0) where XR¹ is methyl-amino, R²is hydrogen and the combination of the radicals R³, R⁴, R^(d) and R^(e)corresponds in each case to one line of Table C.

Table 387

Compounds of the general formula IC (m=0) where XR¹ is methylamino, R²is methyl and the combination of the radicals R³, R⁴, R^(d) and R^(e)corresponds in each case to one line of Table C.

                  TABLE A                                                         ______________________________________                                        No.     R.sup.4  R.sup.5                                                      ______________________________________                                         01     CH.sub.3 C.sub.6 H.sub.5                                                 02 CH.sub.3 2-F--C.sub.6 H.sub.4                                              03 CH.sub.3 3-F--C.sub.6 H.sub.4                                              04 CH.sub.3 4-F--C.sub.6 H.sub.4                                              05 CH.sub.3 2,4-F.sub.2 --C.sub.6 H.sub.3                                     06 CH.sub.3 2,3-F.sub.2 --C.sub.6 H.sub.3                                     07 CH.sub.3 2,4,6-F.sub.3 --C.sub.6 H.sub.2                                   08 CH.sub.3 C.sub.6 F.sub.5                                                   09 CH.sub.3 2-Cl--C.sub.6 H.sub.4                                             10 CH.sub.3 3-Cl--C.sub.6 H.sub.4                                             11 CH.sub.3 4-Cl--C.sub.6 H.sub.4                                             12 CH.sub.3 2,3-Cl.sub.2 --C.sub.6 H.sub.3                                    13 CH.sub.3 2,4-Cl.sub.2 --C.sub.6 H.sub.3                                    14 CH.sub.3 2,5-Cl.sub.2 --C.sub.6 H.sub.3                                    15 CH.sub.3 2,6-Cl.sub.2 --C.sub.6 H.sub.3                                    16 CH.sub.3 3,4-Cl.sub.2 --C.sub.6 H.sub.3                                    17 CH.sub.3 3,5-Cl.sub.2 --C.sub.6 H.sub.3                                    18 CH.sub.3 2,3,4-Cl.sub.3 --C.sub.6 H.sub.2                                  19 CH.sub.3 2,3,5-Cl.sub.3 --C.sub.6 H.sub.2                                  20 CH.sub.3 2,3,6-Cl.sub.3 --C.sub.6 H.sub.2                                  21 CH.sub.3 2,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                  22 CH.sub.3 2,4,6-Cl.sub.3 --C.sub.6 H.sub.2                                  23 CH.sub.3 3,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                  24 CH.sub.3 2,3,4,6-Cl.sub.4 --C.sub.6 H                                      25 CH.sub.3 2,3,5,6-Cl.sub.4 --C.sub.6 H                                      26 CH.sub.3 C.sub.6 Cl.sub.5                                                  27 CH.sub.3 2-Br--C.sub.6 H.sub.4                                             28 CH.sub.3 3-Br--C.sub.6 H.sub.4                                             29 CH.sub.3 4-Br--C.sub.6 H.sub.4                                             30 CH.sub.3 2,4-Br.sub.2 --C.sub.6 H.sub.3                                    31 CH.sub.3 2,5-Br.sub.2 --C.sub.6 H.sub.3                                    32 CH.sub.3 2,6-Br.sub.2 --C.sub.6 H.sub.3                                    33 CH.sub.3 2,4,6-Br.sub.3 --C.sub.6 H.sub.2                                  34 CH.sub.3 C.sub.6 Br.sub.5                                                  35 CH.sub.3 2-I--C.sub.6 H.sub.4                                              36 CH.sub.3 3-I--C.sub.6 H.sub.4                                              37 CH.sub.3 4-I--C.sub.6 H.sub.4                                              38 CH.sub.3 2,4-I.sub.2 --C.sub.6 H.sub.3                                     39 CH.sub.3 2-Cl, 3-F--C.sub.6 H.sub.3                                        40 CH.sub.3 2-Cl, 4-F--C.sub.6 H.sub.3                                        41 CH.sub.3 2-Cl, 5-F--C.sub.6 H.sub.3                                        42 CH.sub.3 2-Cl, 6-F--C.sub.6 H.sub.3                                        43 CH.sub.3 2-Cl, 3-Br--C.sub.6 H.sub.3                                       44 CH.sub.3 2-Cl, 4-Br--C.sub.6 H.sub.3                                       45 CH.sub.3 2-Cl, 5-Br--C.sub.6 H.sub.3                                       46 CH.sub.3 2-Cl, 6-Br--C.sub.6 H.sub.3                                       47 CH.sub.3 2-Br, 3-Cl--C.sub.6 H.sub.3                                       48 CH.sub.3 2-Br, 4-Cl--C.sub.6 H.sub.3                                       49 CH.sub.3 2-Br, 5-Cl--C.sub.6 H.sub.3                                       50 CH.sub.3 2-Br, 6-Cl--C.sub.6 H.sub.3                                       51 CH.sub.3 2-Br, 3-F--C.sub.6 H.sub.3                                        52 CH.sub.3 2-Br, 4-F--C.sub.6 H.sub.3                                        53 CH.sub.3 2-Br, 5-F--C.sub.6 H.sub.3                                        54 CH.sub.3 2-Br, 6-F--C.sub.6 H.sub.3                                        55 CH.sub.3 2-F, 3-Cl--C.sub.6 H.sub.3                                        56 CH.sub.3 2-F, 4-Cl--C.sub.6 H.sub.3                                        57 CH.sub.3 2-F, 5-Cl--C.sub.6 H.sub.3                                        58 CH.sub.3 4-F, 3-Cl--C.sub.6 H.sub.3                                        59 CH.sub.3 5-F, 3-Cl--C.sub.6 H.sub.3                                        60 CH.sub.3 4-Br, 3-Cl--C.sub.6 H.sub.3                                       61 CH.sub.3 5-Br, 3-Cl--C.sub.6 H.sub.3                                       62 CH.sub.3 3-F, 4-Cl--C.sub.6 H.sub.3                                        63 CH.sub.3 3-F, 4-Br--C.sub.6 H.sub.3                                        64 CH.sub.3 3-Br, 4-Cl--C.sub.6 H.sub.3                                       65 CH.sub.3 4-F, 3-Br--C.sub.6 H.sub.3                                        66 CH.sub.3 2,6-Cl.sub.2, 4-Br--C.sub.6 H.sub.2                               67 CH.sub.3 2-CH.sub.3 --C.sub.6 H.sub.4                                      68 CH.sub.3 3-CH.sub.3 --C.sub.6 H.sub.4                                      69 CH.sub.3 4-CH.sub.3 --C.sub.6 H.sub.4                                      70 CH.sub.3 2,3-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                            71 CH.sub.3 2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                            72 CH.sub.3 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                            73 CH.sub.3 2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                            74 CH.sub.3 3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                            75 CH.sub.3 3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                            76 CH.sub.3 2,3,4-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                          77 CH.sub.3 2,3,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                          78 CH.sub.3 2,3,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                          79 CH.sub.3 2,4,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                          80 CH.sub.3 2,4,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                          81 CH.sub.3 3,4,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                          82 CH.sub.3 2,3,4,6-(CH.sub.3).sub.4 --C.sub.6 H                              83 CH.sub.3 2,3,5,6-(CH.sub.3).sub.4 --C.sub.6 H                              84 CH.sub.3 C.sub.6 (CH.sub.3).sub.5                                          85 CH.sub.3 2-C.sub.2 H.sub.5 --C.sub.6 H.sub.4                               86 CH.sub.3 3-C.sub.2 H.sub.5 --C.sub.6 H.sub.4                               87 CH.sub.3 4-C.sub.2 H.sub.5 --C.sub.6 H.sub.4                               88 CH.sub.3 2,4-(C.sub.2 H.sub.5).sub.2 --C.sub.6 H.sub.3                     89 CH.sub.3 2,6-(C.sub.2 H.sub.5).sub.2 --C.sub.6 H.sub.3                     90 CH.sub.3 3,5-(C.sub.2 H.sub.5).sub.2 --C.sub.6 H.sub.3                     91 CH.sub.3 2,4,6-(C.sub.2 H.sub.5).sub.3 --C.sub.6 H.sub.3                   92 CH.sub.3 2-n-C.sub.3 H.sub.7 --C.sub.6 H.sub.4                             93 CH.sub.3 3-n-C.sub.3 H.sub.7 --C.sub.6 H.sub.4                             94 CH.sub.3 4-n-C.sub.3 H.sub.7 --C.sub.6 H.sub.4                             95 CH.sub.3 2-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.4                             96 CH.sub.3 3-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.4                             97 CH.sub.3 4-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.4                             98 CH.sub.3 2,4-(i-C.sub.3 H.sub.7).sub.2 --C.sub.6 H.sub.3                   99 CH.sub.3 2,6-(i-C.sub.3 H.sub.7).sub.2 --C.sub.6 H.sub.3                  100 CH.sub.3 3,5-(i-C.sub.3 H.sub.7).sub.2 --C.sub.6 H.sub.3                  101 CH.sub.3 2-s-C.sub.4 H.sub.9 --C.sub.6 H.sub.4                            102 CH.sub.3 3-s-C.sub.4 H.sub.9 --C.sub.6 H.sub.4                            103 CH.sub.3 4-s-C.sub.4 H.sub.9 --C.sub.6 H.sub.4                            104 CH.sub.3 2-t-C.sub.4 H.sub.9 --C.sub.6 H.sub.4                            105 CH.sub.3 3-t-C.sub.4 H.sub.9 --C.sub.6 H.sub.4                            106 CH.sub.3 4-t-C.sub.4 H.sub.9 --C.sub.6 H.sub.4                            107 CH.sub.3 4-n-C.sub.9 H.sub.19 --C.sub.6 H.sub.4                           108 CH.sub.3 2-CH.sub.3, 4-t-C.sub.4 H.sub.9 --C.sub.6 H.sub.3                109 CH.sub.3 2-CH.sub.3, 6-t-C.sub.4 H.sub.9 --C.sub.6 H.sub.3                110 CH.sub.3 2-CH.sub.3, 4-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.3                111 CH.sub.3 2-CH.sub.3, 5-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.3                112 CH.sub.3 3-CH.sub.3, 4-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.3                113 CH.sub.3 2-c-C.sub.6 H.sub.11 --C.sub.6 H.sub.4                           114 CH.sub.3 3-c-C.sub.6 H.sub.11 --C.sub.6 H.sub.4                           115 CH.sub.3 4-c-C.sub.6 H.sub.11 --C.sub.6 H.sub.4                           116 CH.sub.3 2-Cl, 4-C.sub.6 H.sub.5 --C.sub.6 H.sub.3                        117 CH.sub.3 2-Br, 4-C.sub.6 H.sub.5 --C.sub.6 H.sub.3                        118 CH.sub.3 2-OCH.sub.3 --C.sub.6 H.sub.4                                    119 CH.sub.3 3-OCH.sub.3 --C.sub.6 H.sub.4                                    120 CH.sub.3 4-OCH.sub.3 --C.sub.6 H.sub.4                                    121 CH.sub.3 2-OC.sub.2 H.sub.5 --C.sub.6 H.sub.4                             122 CH.sub.3 3-OC.sub.2 H.sub.5 --C.sub.6 H.sub.4                             123 CH.sub.3 4-OC.sub.2 H.sub.5 --C.sub.6 H.sub.4                             124 CH.sub.3 2-O-n-C.sub.3 H.sub.7 --C.sub.6 H.sub.4                          125 CH.sub.3 3-O-n-C.sub.3 H.sub.7 --C.sub.6 H.sub.4                          126 CH.sub.3 4-O-n-C.sub.3 H.sub.7 --C.sub.6 H.sub.4                          127 CH.sub.3 2-O-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.4                          128 CH.sub.3 3-O-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.4                          129 CH.sub.3 4-O-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.4                          130 CH.sub.3 2-O-n-C.sub.6 H.sub.13 --C.sub.6 H.sub.4                         131 CH.sub.3 3-O-n-C.sub.6 H.sub.13 --C.sub.6 H.sub.4                         132 CH.sub.3 4-O-n-C.sub.6 H.sub.13 --C.sub.6 H.sub.4                         133 CH.sub.3 2-OCH.sub.2 C.sub.6 H.sub.5 -C.sub.6 H.sub.4                     134 CH.sub.3 3-OCH.sub.2 C.sub.6 H.sub.5 --C.sub.6 H.sub.4                    135 CH.sub.3 4-OCH.sub.2 C.sub.6 H.sub.5 --C.sub.6 H.sub.4                    136 CH.sub.3 2-O(CH.sub.2).sub.2 C.sub.6 H.sub.5 --C.sub.6 H.sub.4                            137 CH.sub.3 4-O(CH.sub.2).sub.2 C.sub.6 H.sub.5--C.sub.                     6 H.sub.4                                                      138 CH.sub.3 2,3-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                          139 CH.sub.3 2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                          140 CH.sub.3 2,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                          141 CH.sub.3 2,6-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                          142 CH.sub.3 3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                          143 CH.sub.3 3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                          144 CH.sub.3 2-O-t-C.sub.4 H.sub.9 --C.sub.6 H.sub.4                          145 CH.sub.3 3-O-t-C.sub.4 H.sub.9 --C.sub.6 H.sub.4                          146 CH.sub.3 4-O-t-C.sub.4 H.sub.9 --C.sub.6 H.sub.4                          147 CH.sub.3 3-(3'-Cl-C.sub.6 H.sub.4)--C.sub.6 H.sub.4                       148 CH.sub.3 4-(4'-Cl-C.sub.6 H.sub.4)--C.sub.6 H.sub.4                       149 CH.sub.3 2-OC.sub.6 H.sub.5 --C.sub.6 H.sub.4                             150 CH.sub.3 3-OC.sub.6 H.sub.5 --C.sub.6 H.sub.4                             151 CH.sub.3 4-OC.sub.6 H.sub.5 --C.sub.6 H.sub.4                             152 CH.sub.3 2-O-(2'-F--C.sub.6 H.sub.4)--C.sub.6 H.sub.4                     153 CH.sub.3 3-O-(3'-Cl--C.sub.6 H.sub.4)--C.sub.6 H.sub.4                    154 CH.sub.3 4-O-(4'-CH.sub.3 --C.sub.6 H.sub.4)--C.sub.6 H.sub.4                             155 CH.sub.3 2,3,6-(CH.sub.3).sub.3, 4-F--C.sub.6 H                           156 CH.sub.3 2,3,6-(CH.sub.3).sub.3, 4-Cl--C.sub.6 H                          157 CH.sub.3 2,3,6-(CH.sub.3).sub.3, 4-Br--C.sub.6 H                          158 CH.sub.3 2,4-(CH.sub.3).sub.2, 6-F--C.sub.6 H.sub.2       159 CH.sub.3 2,4-(CH.sub.3).sub.2, 6-Cl--C.sub.6 H.sub.2                      160 CH.sub.3 2,4-(CH.sub.3).sub.2, 6-Br--C.sub.6 H.sub.2                      161 CH.sub.3 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3 --C.sub.6 H.sub.2                          162 CH.sub.3 2-Cl, 4-NO.sub.2 --C.sub.6 H.sub.3                               163 CH.sub.3 4-Cl, 2-NO.sub.2 --C.sub.6 H.sub.3                               164 CH.sub.3 2-OCH.sub.3, 4-NO.sub.2 --C.sub.6 H.sub.3                        165 CH.sub.3 2,4-Cl.sub.2, 5-NO.sub.2 --C.sub.6 H.sub.2       166 CH.sub.3 2,4-Cl.sub.2, 6-NO.sub.2 --C.sub.6 H.sub.2                       167 CH.sub.3 2,6-Cl.sub.2, 4-NO.sub.2 --C.sub.6 H.sub.2                       168 CH.sub.3 2,6-Br.sub.2, 4-NO.sub.2 --C.sub.6 H.sub.2                       169 CH.sub.3 2,6-I.sub.2, 4-NO.sub.2 --C.sub.6 H.sub.2                        170 CH.sub.3 2-CH.sub.3, 4-Cl, 5-i-C.sub.3 H.sub.7 --C.sub.6 H.sub.2                          171 CH.sub.3 2-CO.sub.2 CH.sub.3 --C.sub.6 H.sub.4                            172 CH.sub.3 3-CO.sub.2 CH.sub.3 --C.sub.6 H.sub.4                            173 CH.sub.3 4-CO.sub.2 CH.sub.3 --C.sub.6 H.sub.4                            174 CH.sub.3 2-CH.sub.2 OCH.sub.3 --C.sub.6 H.sub.4                           175 CH.sub.3 3-CH.sub.2 OCH.sub.3 --C.sub.6 H.sub.4                           176 CH.sub.3 4-CH.sub.2 OCH.sub.3 --C.sub.6 H.sub.4                           177 CH.sub.3 2-CH.sub.3, 4-CO-i-C.sub.3 H.sub.7                              --C.sub.6 H.sub.3                                              178 CH.sub.3 2-CH.sub.3, 4-C(CH.sub.3)=NOCH.sub.3 --C.sub.6 H.sub.3                           179 CH.sub.3 2-CH.sub.3, 4-C(CH.sub.3)=NOC.sub.2                             H.sub.5 --C.sub.6 H.sub.3                                      180 CH.sub.3 2-CH.sub.3, 4-C(CH.sub.3)=NO-n-C.sub.3 H.sub.7 --C.sub.6                        H.sub.3                                                        181 CH.sub.3 2-CH.sub.3, 4-C(CH.sub.3)=NO-i-C.sub.3 H.sub.7 --C.sub.6                        H.sub.3                                                        182 CH.sub.3 2,5-(CH.sub.3).sub.2, 4-C(CH.sub.3)=NOCH.sub.3 --C.sub.6                        H.sub.2                                                        183 CH.sub.3 2,5-(CH.sub.3).sub.2, 4-C(CH.sub.3)=NOC.sub.2 H.sub.5                           --C.sub.6 H.sub.2                                              184 CH.sub.3 2,5-(CH.sub.3).sub.2, 4-C(CH.sub.3)=NO-n-C.sub.3 H.sub.7                        --C.sub.6 H.sub.2                                              185 CH.sub.3 2,5-(CH.sub.3).sub.2, 4-C(CH.sub.3)=NO-i-C.sub.3 H.sub.7                        --C.sub.6 H.sub.2                                              186 CH.sub.3 2-C.sub.6 H.sub.5 --C.sub.6 H.sub.4                              187 CH.sub.3 3-C.sub.6 H.sub.5 --C.sub.6 H.sub.4                              188 CH.sub.3 4-C.sub.6 H.sub.5 --C.sub.6 H.sub.4                              189 CH.sub.3 2-(2'-F--C.sub.6 H.sub.4)--C.sub.6 H.sub.4                       190 CH.sub.3 2-CH.sub.3, 5-Br--C.sub.6 H.sub.3                                191 CH.sub.3 2-CH.sub.3, 6-Br--C.sub.6 H.sub.3                                192 CH.sub.3 3-CH.sub.3, 2-Cl--C.sub.6 H.sub.3                                193 CH.sub.3 4-CH.sub.3, 2-Cl--C.sub.6 H.sub.3                                194 CH.sub.3 5-CH.sub.3, 2-Cl--C.sub.6 H.sub.3                                195 CH.sub.3 3-CH.sub.3, 2-F--C.sub.6 H.sub.3                                 196 CH.sub.3 4-CH.sub.3, 2-F--C.sub.6 H.sub.3                                 197 CH.sub.3 5-CH.sub.3, 2-F--C.sub.6 H.sub.3                                 198 CH.sub.3 3-CH.sub.3, 2-Br--C.sub.6 H.sub.3                                199 CH.sub.3 4-CH.sub.3, 2-Br--C.sub.6 H.sub.3                                200 CH.sub.3 5-CH.sub.3, 2-Br--C.sub.6 H.sub.3                                201 CH.sub.3 3-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                202 CH.sub.3 3-CH.sub.3, 5-Cl--C.sub.6 H.sub.3                                203 CH.sub.3 3-CH.sub.3, 4-F--C.sub.6 H.sub.3                                 204 CH.sub.3 3-CH.sub.3, 5-F--C.sub.6 H.sub.3                                 205 CH.sub.3 3-CH.sub.3, 4-Br--C.sub.6 H.sub.3                                206 CH.sub.3 3-CH.sub.3, 5-Br--C.sub.6 H.sub.3                                207 CH.sub.3 4-CH.sub.3, 3-F--C.sub.6 H.sub.3                                 208 CH.sub.3 4-CH.sub.3, 3-Cl--C.sub.6 H.sub.3                                209 CH.sub.3 4-CH.sub.3, 3-Br--C.sub.6 H.sub.3                                210 CH.sub.3 4,5-(CH.sub.3).sub.2, 2-Cl--C.sub.6 H.sub.2                      211 CH.sub.3 4,5-(CH.sub.3).sub.2, 2-Br--C.sub.6 H.sub.2                      212 CH.sub.3 3,5-(CH.sub.3).sub.2, 2-Cl--C.sub.6 H.sub.2                      213 CH.sub.3 3,5-(CH.sub.3).sub.2, 2-Br--C.sub.6 H.sub.2                      214 CH.sub.3 2,6-Cl.sub.2, 4-CH.sub.4 --C.sub.6 H.sub.3                       215 CH.sub.3 2,6-F.sub.2, 4-CH.sub.4 --C.sub.6 H.sub.3                        216 CH.sub.3 2,6-Br.sub.2, 4-CH.sub.4 --C.sub.6 H.sub.3                       217 CH.sub.3 2,4-Br.sub.2, 6-CH.sub.4 --C.sub.6 H.sub.3                       218 CH.sub.3 2,4-F.sub.2, 6-CH.sub.4 --C.sub.6 H.sub.3                        219 CH.sub.3 2,4-Cl.sub.2, 6-CH.sub.4 --C.sub.6 H.sub.3                       220 CH.sub.3 2,6-(CH.sub.3).sub.2, 4-F--C.sub.6 H.sub.2                       221 CH.sub.3 2,6-(CH.sub.3).sub.2, 4-Cl--C.sub.6 H.sub.2                      222 CH.sub.3 2,6-(CH.sub.3).sub.2, 4-Br--C.sub.6 H.sub.2                      223 CH.sub.3 3,5-(CH.sub.3).sub.2, 4-F--C.sub.6 H.sub.2                       224 CH.sub.3 3,5-(CH.sub.3).sub.2, 4-Cl--C.sub.6 H.sub.2                      225 CH.sub.3 3,5-(CH.sub.3).sub.2, 4-Br--C.sub.6 H.sub.2                      226 CH.sub.3 2-CF.sub.3 --C.sub.6 H.sub.4                                     227 CH.sub.3 3-CF.sub.3 --C.sub.6 H.sub.4                                     228 CH.sub.3 4-CF.sub.3 --C.sub.6 H.sub.4                                     229 CH.sub.3 2-OCF.sub.3 --C.sub.6 H.sub.4                                    230 CH.sub.3 3-OCF.sub.3 --C.sub.6 H.sub.4                                    231 CH.sub.3 4-OCF.sub.3 --C.sub.6 H.sub.4                                    232 CH.sub.3 3-OCH.sub.2 CHF.sub.2 --C.sub.6 H.sub.4                          233 CH.sub.3 2-NO.sub.2 --C.sub.6 H.sub.4                                     234 CH.sub.3 3-NO.sub.2 --C.sub.6 H.sub.4                                     235 CH.sub.3 4-NO.sub.2 --C.sub.6 H.sub.4                                     236 CH.sub.3 2-CN--C.sub.6 H.sub.4                                            237 CH.sub.3 3-CN--C.sub.6 H.sub.4                                            238 CH.sub.3 4-CN--C.sub.6 H.sub.4                                            239 CH.sub.3 2-CH.sub.3, 3-Cl--C.sub.6 H.sub.3                                240 CH.sub.3 2-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                241 CH.sub.3 2-CH.sub.3, 5-Cl--C.sub.6 H.sub.3                                242 CH.sub.3 2-CH.sub.3, 6-Cl--C.sub.6 H.sub.3                                243 CH.sub.3 2-CH.sub.3, 3-F--C.sub.6 H.sub.3                                 244 CH.sub.3 2-CH.sub.3, 4-F--C.sub.6 H.sub.3                                 245 CH.sub.3 2-CH.sub.3, 5-F--C.sub.6 H.sub.3                                 246 CH.sub.3 2-CH.sub.3, 6-F--C.sub.6 H.sub.3                                 247 CH.sub.3 2-CH.sub.3, 3-Br--C.sub.6 H.sub.3                                248 CH.sub.3 2-CH.sub.3, 4-Br--C.sub.6 H.sub.3                                249 CH.sub.3 2-CH.sub.3, 5-Br--C.sub.6 H.sub.3                                250 CH.sub.3 2-CH.sub.3, 6-Br--C.sub.6 H.sub.3                                251 CH.sub.3 2,5-F.sub.2 --C.sub.6 H.sub.3                                    252 CH.sub.3 2,6-F.sub.2 --C.sub.6 H.sub.3                                    253 CH.sub.3 3,4-F.sub.2 --C.sub.6 H.sub.3                                    254 CH.sub.3 3,5-F.sub.2 --C.sub.6 H.sub.3                                  ______________________________________                                         n = neo; i = iso; s = secondary; t = tertiary; c = cyclo                 

                  TABLE B                                                         ______________________________________                                        No.           R.sup.x                                                         ______________________________________                                         01           H                                                                  02 2-F                                                                        03 3-F                                                                        04 4-F                                                                        05 2,4-F.sub.2                                                                06 2,3-F.sub.2                                                                07 2,4,6-F.sub.3                                                              08 2,3,4,5,6-F.sub.5                                                          09 2-Cl                                                                       10 3-Cl                                                                       11 4-Cl                                                                       12 2,3-Cl.sub.2                                                               13 2,4-Cl.sub.2                                                               14 2,5-Cl.sub.2                                                               15  2,6-Cl.sub.2                                                              16 3,4-Cl.sub.2                                                               17 3,5-Cl.sub.2                                                               18 2,3,4-Cl.sub.3                                                             19 2,3,5-Cl.sub.3                                                             20 2,3,6-Cl.sub.3                                                             21 2,4,5-Cl.sub.3                                                             22 2,4,6-Cl.sub.3                                                             23 3,4,5-Cl.sub.3                                                             24 2,3,4,6-Cl.sub.4                                                           25 2,3,5,6-Cl.sub.4                                                           26 2,3,4,5,6-Cl.sub.5                                                         27 2-Br                                                                       28 3-Br                                                                       29 4-Br                                                                       30 2,4-Br.sub.2                                                               31 2,5-Br.sub.2                                                               32 2,6-Br.sub.2                                                               33 2,4,6-Br.sub.3                                                             34 2,3,4,5,6-Br.sub.5                                                         35 2-I                                                                        36 3-I                                                                        37 4-I                                                                        38 2,4-I.sub.2                                                                39 2-Cl, 3-F                                                                  40 2-Cl, 4-F                                                                  41 2-Cl, 5-F                                                                  42 2-Cl, 6-F                                                                  43 2-Cl, 3-Br                                                                 44 2-Cl, 4-Br                                                                 45 2-Cl, 5-Br                                                                 46 2-Cl, 6-Br                                                                 47 2-Br, 3-Cl                                                                 48 2-Br, 4-Cl                                                                 49 2-Br, 5-Cl                                                                 50 2-Br, 6-Cl                                                                 51 2-Br, 3-F                                                                  52 2-Br, 4-F                                                                  53 2-Br, 5-F                                                                  54 2-Br, 6-F                                                                  55 2-F, 3-Cl                                                                  56 2-F, 4-Cl                                                                  57 2-F, 5-Cl                                                                  58 4-F, 3-Cl                                                                  59 5-F, 3-Cl                                                                  60 4-Br, 3-Cl                                                                 61 5-Br, 3-Cl                                                                 62 3-F, 4-Cl                                                                  63 3-F, 4-Br                                                                  64 3-Br, 4-Cl                                                                 65 4-F, 3-Br                                                                  66 2,6-Cl.sub.2, 4-Br                                                         67 2-CH.sub.3                                                                 68 3-CH.sub.3                                                                 69 4-CH.sub.3                                                                 70 2,3-(CH.sub.3).sub.2                                                       71 2,4-(CH.sub.3).sub.2                                                       72 2,5-(CH.sub.3).sub.2                                                       73 2,6-(CH.sub.3).sub.2                                                       74 3,4-(CH.sub.3).sub.2                                                       75 3,5-(CH.sub.3).sub.2                                                       76 2,3,4-(CH.sub.3).sub.3                                                     77 2,3,5-(CH.sub.3).sub.3                                                     78 2,3,6-(CH.sub.3).sub.3                                                     79 2,4,5-(CH.sub.3).sub.3                                                     80 2,4,6-(CH.sub.3).sub.3                                                     81 3,4,5-(CH.sub.3).sub.3                                                     82 2,3,4,6-(CH.sub.3).sub.4                                                   83 2,3,5,6-(CH.sub.3).sub.4                                                   84 2,3,4,5,6-(CH.sub.3)5                                                      85 2-C.sub.2 H.sub.5                                                          86 3-C.sub.2 H.sub.5                                                          87 4-C.sub.2 H.sub.5                                                          88 2,4-(C.sub.2 H.sub.5)2                                                     89 2,6-(C.sub.2 H.sub.5)2                                                     90 3,5-(C.sub.2 H.sub.5)2                                                     91 2,4,6-(C.sub.2 H.sub.5)3                                                   92 2-n-C.sub.3 H.sub.7                                                        93 3-n-C.sub.3 H.sub.7                                                        94 4-n-C.sub.3 H.sub.7                                                        95 2-i-C.sub.3 H.sub.7                                                        96 3-i-C.sub.3 H.sub.7                                                        97 4-i-C.sub.3 H.sub.7                                                        98 2,4-(i-C.sub.3 H.sub.7)2                                                   99 2,6-(i-C.sub.3 H.sub.7)2                                                  100 3,5-(i-C.sub.3 H.sub.7)2                                                  101 2-s-C.sub.4 H.sub.9                                                       102 3-s-C.sub.4 H.sub.9                                                       103 4-s-C.sub.4 H.sub.9                                                       104 2-t-C.sub.4 H.sub.9                                                       105 3-t-C.sub.4 H.sub.9                                                       106 4-t-C.sub.4 H.sub.9                                                       107 4-n-C.sub.9 H.sub.19                                                      108 2-CH.sub.3, 4-t-C.sub.4 H.sub.9                                           109 2-CH.sub.3, 6-t-C.sub.4 H.sub.9                                           110 2-CH.sub.3, 4-i-C.sub.3 H.sub.7                                           111 2-CH.sub.3, 5-i-C.sub.3 H.sub.7                                           112 3-CH.sub.3, 4-i-C.sub.3 H.sub.7                                           113 2-c-C.sub.6 H.sub.11                                                      114 3-c-C.sub.6 H.sub.11                                                      115 4-c-C.sub.6 H.sub.11                                                      116 2-Cl, 4-C.sub.6 H.sub.5                                                   117 2-Br, 4-C.sub.6 H.sub.5                                                   118 2-OCH.sub.3                                                               119 3-OCH.sub.3                                                               120 4-OCH.sub.3                                                               121 2-OC.sub.2 H.sub.5                                                        122 3-OC.sub.2 H.sub.5                                                        123 4-OC.sub.2 H.sub.5                                                        124 2-O-n-C.sub.3 H.sub.7                                                     125 3-O-n-C.sub.3 H.sub.7                                                     126 4-O-n-C.sub.3 H.sub.7                                                     127 2-O-i-C.sub.3 H.sub.7                                                     128 3-O-i-C.sub.3 H.sub.7                                                     129 4-O-i-C.sub.3 H.sub.7                                                     130 2-O-n-C.sub.6 H.sub.13                                                    131 3-O-n-C.sub.6 H.sub.13                                                    132 4-O-n-C.sub.6 H.sub.13                                                    133 2-OCH.sub.2 C.sub.6 H.sub.5                                               134 3-OCH.sub.2 C.sub.6 H.sub.5                                               135 4-OCH.sub.2 C.sub.6 H.sub.5                                               136 2-O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                       137 4-O(CH.sub.2).sub.2 C.sub.6 H.sub.5                                       138 2,3-(OCH.sub.3).sub.2                                                     139 2,4-(OCH.sub.3).sub.2                                                     140 2,5-(OCH.sub.3).sub.2                                                     141 2,6-(OCH.sub.3).sub.2                                                     142 3,4-(OCH.sub.3).sub.2                                                     143 3,5-(OCH.sub.3).sub.2                                                     144 2-O-t-C.sub.4 H.sub.9                                                     145 3-O-t-C.sub.4 H.sub.9                                                     146 4-O-t-C.sub.4 H.sub.9                                                     147 3-(3'-Cl-C.sub.6 H.sub.4)                                                 148 4-(4'-Cl-C.sub.6 H.sub.4)                                                 149 2-OC.sub.6 H.sub.5                                                        150 3-OC.sub.6 H.sub.5                                                        151 4-OC.sub.6 H.sub.5                                                        152 2-O-(2'-F--C.sub.6 H.sub.4)                                               153 3-O-(3'-Cl--C.sub.6 H.sub.4)                                              154 4-O-(4'-CH.sub.3 --C.sub.6 H.sub.4)                                       155 2,3,6-(CH.sub.3).sub.3, 4-F                                               156 2,3,6-(CH.sub.3).sub.3, 4-Cl                                              157 2,3,6-(CH.sub.3).sub.3, 4-Br                                              158 2,4-(CH.sub.3).sub.2, 6-F                                                 159 2,4-(CH.sub.3).sub.2, 6-Cl                                                160 2,4-(CH.sub.3).sub.2, 6-Br                                                161 2-i-C.sub.3 H.sub.7, 4-Cl, 5-CH.sub.3                                     162 2-Cl, 4-NO.sub.2                                                          163 4-Cl, 2-NO.sub.2                                                          164 2-OCH.sub.3, 4-NO.sub.2                                                   165 2,4-Cl.sub.2, 5-NO.sub.2                                                  166 2,4-Cl.sub.2, 6-NO.sub.2                                                  167 2,6-Cl.sub.2, 4-NO.sub.2                                                  168 2,6-Br.sub.2, 4-NO.sub.2                                                  169 2,6-I.sub.2, 4-NO.sub.2                                                   170 2-CH.sub.3, 4-Cl, 5-i-C.sub.3 H.sub.7                                     171 2-CO.sub.2 CH.sub.3                                                       172 3-CO.sub.2 CH.sub.3                                                       173 4-CO.sub.2 CH.sub.3                                                       174 2-CH.sub.2 OCH.sub.3                                                      175 3-CH.sub.2 OCH.sub.3                                                      176 4-CH.sub.2 OCH.sub.3                                                      177 2-CH.sub.3, 4-CO-i-C.sub.3 H.sub.7                                        178 2-CH.sub.3, 4-C(CH.sub.3)=NOCH.sub.3                                      179 2-CH.sub.3, 4-C(CH.sub.3)=NOC.sub.2 H.sub.5                               180 2-CH.sub.3, 4-C(CH.sub.3)=NO-n-C.sub.3 H.sub.7                            181 2-CH.sub.3, 4-C(CH.sub.3)=NO-i-C.sub.3 H.sub.7                            182 2,5-(CH.sub.3).sub.2, 4-C(CH.sub.3)=NOCH.sub.3                            183 2,5-(CH.sub.3).sub.2, 4-C(CH.sub.3)=NOC.sub.2 H.sub.5                     184 2,5-(CH.sub.3).sub.2, 4-C(CH.sub.3)=NO-n-C.sub.3 H.sub.7                  185 2,5-(CH.sub.3).sub.2, 4-C(CH.sub.3)=NO-i-C.sub.3 H.sub.7                  186 2-C.sub.6 H.sub.5                                                         187 3-C.sub.6 H.sub.5                                                         188 4-C.sub.6 H.sub.5                                                         189 2-(2'-F--C.sub.6 H.sub.4)                                                 190 2-CH.sub.3, 5-Br                                                          191 2-CH.sub.3, 6-Br                                                          192 3-CH.sub.3, 2-Cl                                                          193 4-CH.sub.3, 2-Cl                                                          194 5-CH.sub.3, 2-Cl                                                          195 3-CH.sub.3, 2-F                                                           196 4-CH.sub.3, 2-F                                                           197 5-CH.sub.3, 2-F                                                           198 3-CH.sub.3, 2-Br                                                          199 4-CH.sub.3, 2-Br                                                          200 5-CH.sub.3, 2-Br                                                          201 3-CH.sub.3, 4-Cl                                                          202 3-CH.sub.3, 5-Cl                                                          203 3-CH.sub.3, 4-F                                                           204 3-CH.sub.3, 5-F                                                           205 3-CH.sub.3, 4-Br                                                          206 3-CH.sub.3, 5-Br                                                          207 4-CH.sub.3, 3-F                                                           208 4-CH.sub.3, 3-Cl                                                          209 4-CH.sub.3, 3-Br                                                          210 4,5-(CH.sub.3).sub.2, 2-Cl                                                211 4,5-(CH.sub.3).sub.2, 2-Br                                                212 3,5-(CH.sub.3).sub.2, 2-Cl                                                213 3,5-(CH.sub.3).sub.2, 2-Br                                                214 2,6-Cl.sub.2, 4-CH.sub.4                                                  215 2,6-F.sub.2, 4-CH.sub.4                                                   216 2,6-Br.sub.2, 4-CH.sub.4                                                  217 2,4-Br.sub.2, 6-CH.sub.4                                                  218 2,4-F.sub.2, 6-CH.sub.4                                                   219 2,4-Cl.sub.2, 6-CH.sub.4                                                  220 2,6-(CH.sub.3).sub.2, 4-F                                                 221 2,6-(CH.sub.3).sub.2, 4-Cl                                                222 2,6-(CH.sub.3).sub.2, 4-Br                                                230 3-OCF.sub.3                                                               231 4-OCF.sub.3                                                               232 3-OCH.sub.2 CHF.sub.2                                                     233 2-NO.sub.2                                                                234 3-NO.sub.2                                                                235 4-NO.sub.2                                                                236 2-CN                                                                      237 3-CN                                                                      238 4-CN                                                                      239 2-CH.sub.3, 3-Cl                                                          240 2-CH.sub.3, 4-Cl                                                          241 2-CH.sub.3, 5-Cl                                                          242 2-CH.sub.3, 6-Cl                                                          243 2-CH.sub.3, 3-F                                                           244 2-CH.sub.3, 4-F                                                           245 2-CH.sub.3, 5-F                                                           246 2-CH.sub.3, 6-F                                                           247 2-CH.sub.3, 3-Br                                                          248 2-CH.sub.3, 4-Br                                                          249 2-CH.sub.3, 5-Br                                                          250 2-CH.sub.3, 6-Br                                                          251 2,5-F.sub.2                                                               252 2,6-F.sub.2                                                               253 3,4-F.sub.2                                                               254 3,5-F.sub.2                                                             ______________________________________                                         n = neo; i = iso; s = secondary; t = tertiary; c = cyclo                 

                  TABLE C                                                         ______________________________________                                        No.  R.sup.3    R.sup.4   R.sup.d  R.sup.e                                    ______________________________________                                        01   H          CH.sub.3  CH.sub.3 CH.sub.3                                     02 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3                                        03 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3                                 04 n-C.sub.3 H.sub.7 CH.sub.3 CH.sub.3 CH.sub.3                               05 i-C.sub.3 H.sub.7 CH.sub.3 CH.sub.3 CH.sub.3                               06 c-C.sub.3 H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3                               07 pyridin-2-yl CH.sub.3 CH.sub.3 CH.sub.3                                    08 pyridin-3-yl CH.sub.3 CH.sub.3 CH.sub.3                                    09 pyridin-4-yl CH.sub.3 CH.sub.3 CH.sub.3                                    10 5-CH.sub.3 -isox- CH.sub.3 CH.sub.3 CH.sub.3                                azol-3-yl                                                                    11 phenyl CH.sub.3 CH.sub.3 CH.sub.3                                          12 CH.sub.3 H CH.sub.3 CH.sub.3                                               13 CH.sub.3 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3                                 14 CH.sub.3 n-C.sub.3 H.sub.7 CH.sub.3 CH.sub.3                               15 CH.sub.3 i-C.sub.3 H.sub.7 CH.sub.3 CH.sub.3                               16 CH.sub.3 c-C.sub.3 H.sub.5 CH.sub.3 CH.sub.3                               17 CH.sub.3 pyridin-2-yl CH.sub.3 CH.sub.3                                    18 CH.sub.3 pyridin-3-yl CH.sub.3 CH.sub.3                                    19 CH.sub.3 pyridin-4-yl CH.sub.3 CH.sub.3                                    20 CH.sub.3 5-CH.sub.3 -isox- CH.sub.3 CH.sub.3                                 azol-3-yl                                                                   21 CH.sub.3 phenyl CH.sub.3 CH.sub.3                                          22 CH.sub.3 CH.sub.3 H CH.sub.3                                               23 CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 CH.sub.3                                 24 CH.sub.3 CH.sub.3 n-C.sub.3 H.sub.7 CH.sub.3                               25 CH.sub.3 CH.sub.3 i-C.sub.3 H.sub.7 CH.sub.3                               26 CH.sub.3 CH.sub.3 c-C.sub.3 H.sub.5 CH.sub.3                               27 CH.sub.3 CH.sub.3 pyridin-2-yl CH.sub.3                                    28 CH.sub.3 CH.sub.3 pyridin-3-yl CH.sub.3                                    29 CH.sub.3 CH.sub.3 pyridin-4-yl CH.sub.3                                    30 CH.sub.3 CH.sub.3 5-CH.sub.3 -isox- CH.sub.3                                  azol-3-yl                                                                  31 CH.sub.3 CH.sub.3 phenyl CH.sub.3                                          32 CH.sub.3 CH.sub.3 CH.sub.3 C.sub.2 H.sub.5                                 33 CH.sub.3 CH.sub.3 CH.sub.3 n-C.sub.3 H.sub.7                               34 CH.sub.3 CH.sub.3 CH.sub.3 i-C.sub.3 H.sub.7                               35 CH.sub.3 CH.sub.3 CH.sub.3 t-C.sub.4 H.sub.9                               36 CH.sub.3 CH.sub.3 CH.sub.3 benzyl                                          37 CH.sub.3 CH.sub.3 CH.sub.3 propargyl                                       38 CH.sub.3 CH.sub.3 CH.sub.3 bromopropargyl                                  39 CH.sub.3 CH.sub.3 CH.sub.3 iodopropargyl                                   30 CH.sub.3 CH.sub.3 CH.sub.3 allyl                                           41 CH.sub.3 CH.sub.3 CH.sub.3 trans-chloro-                                       allyl                                                                     42 CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.3                   ______________________________________                                         n = neo; i = iso; s = secondary; t = tertiary; c = cyclo                 

The present invention also relates to intermediates of the formulae IVand V ##STR9## where R, R³, R⁴, R⁵ and m have the above-mentionedmeanings.

The preparation of compounds IV and V is described on pages 5 to 7.

The compounds I are useful as fungicides.

The compounds I are distinguished by an outstanding activity against awide spectrum of phytopathogenic fungi, in particular from the classesof the Ascomycetes, Phycomycetes and asidiomycetes. Some of them actsystemically and can be employed in crop protection as foliar- andsoil-acting fungicides.

They are especially important for controlling a large number of fungi ona variety of crop plants such as wheat, rye, barley, oats, rice, maize,grass, cotton, soya, coffee, sugar cane, grapevine, fruit species,ornamentals and vegetable species such as cucumbers, beans andcucurbits, and on the seeds of these plants.

Specifically, they are suitable for controlling the following plantdiseases: Erysiphe graminis (powdery mildew) in cereals, Erysiphecichoracearum and Sphaerotheca fuliginea in cucurbits, Podosphaeraleucotricha in apples, Uncinula necator in grapevines, Puccinia speciesin cereals, Rhizoctonia species in cotton, rice and lawns, Ustilagospecies in cereals and sugar cane, Venturia inaequalis (scab) in apples,Helminthosporium species in cereals, Septoria nodorum in wheat, Botrytiscinerea (gray mold) in strawberries, vegetables, ornamentals,grapevines, Cercospora arachidicola in groundnuts, Pseudocercosporellaherpotrichoides in wheat and barley, Pyricularia oryzae in rice,Phytophthora infestans in potatoes and tomatoes, Fusarium andVerticillium species in a variety of plants, Plasmopara viticola ingrapevines, and Alternaria species in vegetables and fruit.

Moreover, the compounds I are suitable for controlling harmful fungi inthe protection of materials (eg. wood, paper, fibers or wovens) and inthe protection of stored products.

The compounds I are used by treating the fungi, or the plants, seeds,materials or the soil to be protected against fungal infection, with afungicidally active amount of the active ingredients. Application iseffected before or after infection of the materials, plants or seeds bythe fungi.

They can be converted into the customary formulations, such assolutions, emulsions, suspensions, dusts, powders, pastes and granules.The use form depends on the intended purpose; in any case, it shouldguarantee fine and uniform distribution of the compound according to theinvention. The formulations are prepared in a known manner, eg. byextending the active ingredient with solvents and/or carriers, ifdesired using emulsifiers and dispersants, it also being possible to useother organic solvents as auxiliary solvents if water is used as thediluent. Suitable auxiliaries are essentially: solvents such asaromatics (eg. xylene), chlorinated aromatics (eg. chlorobenzenes),paraffins (eg. mineral oil fractions), alcohols (eg. methanol, butanol),ketones (eg. cyclohexanone), amines (eg. ethanolamine,dimethylformamide) and water; carriers such as ground natural minerals(eg. kaolins, clays, talc, chalk) and ground synthetic minerals (eg.highly-disperse silica, silicates); emulsifiers such as non-ionic andanionic emulsifiers (eg. polyoxyethylene fatty alcohol ethers,alkylsulfonates and arylsulfonates) and dispersants such aslignin-sulfite waste liquors and methylcellulose.

In general, the fungicidal compositions comprise from 0.1 to 95,preferably 0.5 to 90, % by weight of active ingredient.

The rates of application for use in crop protection are from 0.01 to 2.0kg of active ingredient per ha, depending on the nature of the desiredeffect.

In the case of seed treatment, amounts of active ingredient of from0.001 to 0.1 g, preferably 0.01 to 0.05 g, are generally required perkilogram of seed.

When used in the protection of materials or of stored products, the rateof active ingredient to be applied depends on the type of harmful fungusor the field of application. Usual rates of application in theprotection of materials are, for example, from 0.001 g to 2 kg,preferably 0.005 g to 1 kg, of active ingredient per cubic meter ofmaterial treated.

In their use form as fungicides, the compositions according to theinvention can also be present together with other active ingredients,eg. with herbicides, insecticides, growth regulators, fungicides, orelse with fertilizers.

A mixture with fungicides frequently results in a widened fungicidalspectrum of action.

The following list of fungicides together with which the compoundsaccording to the invention can be used is intended to illustratepossible combinations, but not to impose any limitation:

sulfur, dithiocarbamates and their derivatives, such as irondimethyldithiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate,manganese zinc ethylenediaminebisdithiocarbamate, tetramethylthiuramdisulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate),ammonia complex of zinc (N,N'-propylenebisdithiocarbamate), zinc(N,N'-propylenebisdithiocarbamate), N,N'-polypropylenebis(thiocarbamoyl)disulfide;

nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate,2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate,2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate, diisopropyl5-nitro-isophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate,2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethylphthalimidophosphonothioate,5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole,2,3-dicyano-1,4-dithioanthraquinone,2-thio-1,3-dithiolo[4,5-b]quinoxaline,1-(butylcarbamoyl)-2-benzimidazolecarbamate,2-methoxycarbonylaminobenzimidazole, 2-(2-furyl)benzimidazole,2-((4-thiazolyl)benzimidazole,N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide,N-trichloromethylthiotetrahydrophthalimide,N-trichloromethylthiophthalimide,N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuramide,5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole,2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene,4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone, pyridine-2-thiol1-oxide, 8-hydroxyquinoline or its copper salt,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide,2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide,2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide,2,4,5-trimethylfuran-3-carboxanilide, N-cyclohexyl2,5-dimethylfuran-3-carboxamide,N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide,2-methylbenzanilide, 2-iodobenzanilide,N-2,2,2-trichloro-1-(4-morpholinyl)ethylformamide,piperazine-1,4-diylbis(2,2,2-trichloroethyl)formamide,1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,2,6-dimethyl-N-tridecylmorpholine or its salts,2,6-dimethyl-N-cyclododecylmorpholine or its salts,N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine,N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine,1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea,1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-triazol-1-yl)-2-butanone,1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol,α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine,bis(p-chlorophenyl)-3-pyridinemethanol,1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene,1,2-bis(3-methoxycarbonyl-2-thioureido)benzene,

and a variety of fungicides, such as dodecylguanidine acetate,3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide,hexachlorobenzene,DL-methyl-N-(2,6-dimethylphenyl)-N-(2-furoyl)alaninate,DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)alanine methyl ester,N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone,DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester,5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,3-(3,5-dichlorophenyl)5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin,N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,2-cyano-[N-(ethyl-aminocarbonyl)-2-methoximino]acetamide,1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole,2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol,N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine,1-((bis-(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.

The compounds of the formula I are furthermore suitable for effectivelycontrolling pests from the classes of the insects, arachnids andnematodes. They can be employed as pesticides in crop protection and inthe hygiene, stored-product and veterinary sector.

The harmful insects include, from the order of the lepidopterans(Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabamaargillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographagamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana,Cheimatobia brumata, Choristoneura fumiferana, Choristoneuraoccidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini,Diaphania nitidalis, Diatraea grandiosella, Earias insulana,Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana,Feltia subterranea, Galleria mellonella, Grapholitha funebrana,Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothiszea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeutamalinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygmaexigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletisblancardella, Lobesia botrana, Loxostege stictiKalis, Lymantria dispar,Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestrabrassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea,Pectinophora gossypiella, Peridroma saucia, Phalera bucephala,Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae,Plathypena scabra, Plutella xylostella, Pseudoplusia includens,Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella,Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis,Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana,Trichoplusia ni, Zeiraphera canadensis.

From the order of the beetles (Coleoptera), for example, Agrilussinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallussolstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum,Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchusrufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassidanebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis,Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus,Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata,Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis,Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis,Hypera postica, Ips typographus, Lema bilineata, Lema melanopus,Leptinotarsa decemlineata, Limonius Kalifornicus, Lissorhoptrusoryzophilus, Melanotus communis, Meligethes aeneus, Melolonthahippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchussulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotretachrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotretanemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus,Sitophilus granaria.

From the order of the dipterans (Diptera), for example, Aedes aegypti,Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitiscapitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomyamacellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culexpipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fanniacanicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobiairritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata,Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina,Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Muscadomestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomyahysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata,Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipulaoleracea, Tipula paludosa.

From the order of the thrips (Thysanoptera), for example, Frankliniellafusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothripscitri, Thrips oryzae, Thrips palmi, Thrips tabaci.

From the order of the hymenopterans (Hymenoptera), for example, Athaliarosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta,Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata,Solenopsis invicta.

From the order of the heteropterans (Heteroptera), for example,Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercuscingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistusimpictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lyguspratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyantaperditor.

From the order of the homopterans (Homoptera), for example,Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphisfabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicorynebrassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusiapiceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae,Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megouraviciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi,Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida,Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus,Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphisgraminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteusvitifolii.

From the order of the termites (Isoptera), for example, Kalotermesflavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termesnatalensis.

From the order of the orthopterans (Orthoptera), for example, Achetadomestica, Blatta orientalis, Blattella germanica, Forficulaauricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplusbivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplussanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplanetaamericana, Schistocerca americana, Schistocerca peregrina, Stauronotusmaroccanus, Tachycines asynamorus.

From the class of the Arachnoidea, for example, arachnids (Acarina) suchas Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilusannulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpusphoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychuscarpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodesrubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychuspilosus, Dermanyssus gallinae, Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus,Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus,Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius,Tetranychus urticae.

From the class of the nematodes, for example, root knot nematodes, eg.Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica,cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae,Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stemeelworms and foliar nematodes, eg. Belonolaimus longicaudatus,Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchusmulticinctus, Longidorus elongatus, Radopholus similis, Rotylenchusrobustus, Trichodorus primitivus, Tylenchorhynchus claytoni,Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenchus penetrans,Pratylenchus curvitatus, Pratylenchus goodeyi.

The active ingredients can be used as such, in the form of theirformulations or the use forms prepared therefrom, for example in theform of directly sprayable solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dusts, materials forspreading or granules by means of spraying, atomizing, dusting,spreading or pouring. The use forms depend entirely on the intendedpurposes; in any case, they should guarantee the finest possibledistribution of the active ingredients according to the invention.

The concentrations of active ingredient in the ready-to-use preparationscan be varied within substantial ranges.

In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

The active ingredients can also be used successfully in theultra-low-volume method (ULV), it being possible to apply formulationscomprising over 95% by weight of active ingredient, or even the activeingredient without additives.

The rate of active ingredient to be applied for controlling pests is 0.1to 2.0, preferably 0.2 to 1.0, kg/ha under field conditions.

Substances which are suitable for the preparation of directly sprayablesolutions, emulsions, pastes or oil dispersions are mineral oilfractions of medium to high boiling point such as kerosine or dieseloil, furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, eg. benzene, toluene,xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or theirderivatives, methanol, ethanol, propanol, butanol, chloroform, carbontetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone,and strongly polar solvents, eg. dimethylformamide, dimethyl sulfoxide,N-methylpyrrolidone or water.

Aqueous use forms can be prepared from emulsion concentrates, pastes orwettable powders (sprayable powders, oil dispersions) by adding water.To prepare emulsions, pastes or oil dispersions, the substances, as suchor dissolved in an oil or solvent, can be homogenized in water by meansof a wetting agent, adhesive, dispersant or emulsifier. It is alsopossible to prepare concentrates composed of active ingredient, wettingagent, adhesive, dispersant or emulsifier and, if desired, solvent oroil, which are suitable for dilution with water.

Suitable surfactants are alkali metal, alkaline earth metal and ammoniumsalts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonicacid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids andtheir alkali metal and alkaline earth metal salts, salts of sulfatedfatty alcohol glycol ether, condensates of sulfonated naphthalene andnaphthalene derivatives with formaldehyde, condensates of naphthalene,or of naphthalenesulfonic acid, with phenol and formaldehyde,polyoxyethylene octylphenyl ether, ethoxylated isooctylphenol,octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, laurylalcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite wasteliquors and methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing orgrinding the active ingredients together with a solid carrier.

In general, the formulations comprise from 0.01 to 95% by weight,preferably 0.1 to 90% by weight, of the active ingredient. The activeingredients are employed in a purity of from 90% to 100%, preferably 95%to 100% (according to NMR spectrum).

Examples of formulations are:

I. 5 parts by weight of a compound according to the invention are mixedintimately with 95 parts by weight of finely divided kaolin. This givesa dust which comprises 5% by weight of the active ingredient.

II. 30 parts by weight of a compound according to the invention aremixed intimately with a mixture of 92 parts by weight of pulverulentsilica gel and 8 parts by weight of paraffin oil which had been sprayedonto the surface of this silica gel. This gives a preparation of theactive ingredient which has good adherence properties (comprises 23% byweight of active ingredient).

III. 10 parts by weight of a compound according to the invention aredissolved in a mixture composed of 90 parts by weight of xylene, 6 partsby weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mole ofoleic acid N-monoethanolamide, 2 parts by weight of calciumdodecylbenzenesulfonate and 2 parts by weight of the adduct of 40 mol ofethylene oxide to 1 mole of castor oil (comprises 9% by weight of activeingredient).

IV. 20 parts by weight of a compound according to the invention aredissolved in a mixture composed of 60 parts by weight of cyclohexanone,30 parts by weight of isobutanol, 5 parts by weight of the adduct of 7mol of ethylene oxide and 1 mole of isooctylphenol and 5 parts by weightof the adduct of 40 mol of ethylene oxide to 1 mole of castor oil(comprises 16% by weight of active ingredient).

V. 80 parts by weight of a compound according to the invention are mixedthoroughly with 3 parts by weight of sodiumdiisobutylnaphthalene-alpha-sulfonate, 10 parts by weight of the sodiumsalt of a lignosulfonic acid from a sulfite waste liquor and 7 parts byweight of pulverulent silica gel and the mixture is ground in a hammermill (comprises 80% by weight of active ingredient).

VI. 90 parts by weight of a compound according to the invention aremixed with 10 parts by weight of N-methyl-α-pyrrolidone, which gives asolution which is suitable for use in the form of microdrops (comprises90% by weight of active ingredient).

VII. 20 parts by weight of a compound according to the invention aredissolved in a mixture composed of 40 parts by weight of cyclohexanone,30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7mol of ethylene oxide and 1 mole of isooctylphenol and 10 parts byweight of the adduct of 40 mol of ethylene oxide and 1 mole of castoroil. Pouring the solution into 100,000 parts by weight of water andfinely distributing it therein gives an aqueous dispersion whichcomprises 0.02% by weight of the active ingredient.

VIII. 20 parts by weight of a compound according to the invention aremixed thoroughly with 3 parts by weight of sodiumdiisobutylnaphthalene-a-sulfonate, 17 parts by weight of the sodium saltof a lignosulfonic acid from a sulfite waste liquor and 60 parts byweight of pulverulent silica gel, and the mixture is ground in a hammermill. Finely distributing the mixture in 20,000 parts by weight of watergives a spray mixture which comprises 0.1% by weight of the activeingredient.

Granules, eg. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active ingredients to solidcarriers. Examples of solid carriers are mineral earths such as silicagel, silicas, silica gels, silicates, talc, kaolin, attaclay, limestone,lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calciumsulfate, magnesium sulfate, magnesium oxide, ground synthetic materials,fertilizers, eg. ammonium sulfate, ammonium phosphate, ammonium nitrateor ureas, and products of vegetable origin, such as cereal meal, treebark meal, wood meal and nutshell meal, cellulose powders and othersolid carriers.

Various types of oils, or herbicides, fungicides, other pesticides, orbactericides, may be added to the active ingredients, if desired alsoimmediately prior to use (tank mix). These can be admixed with thecompositions according to the invention in a weight ratio of 1:10 to10:1.

SYNTHESIS EXAMPLES

The protocols given in the synthesis examples which follow were used,with appropriate modification of the starting compounds, for obtainingother compounds I. The resulting compounds together with physical dataare listed in the table which follows.

1. Preparation of ##STR10##

A mixture of 3.8 g (20 mmol) of N-acetylacetophenone hydrazone in 15 mlof dimethylformamide was treated with 0.6 g (26 mmol) of sodium hydride,a little at a time, and the mixture was stirred until the evolution ofgas had ceased. The resulting mixture was subsequently treated with 8.4g (20 mmol) of methyl N-methoxy-N-(o-bromomethylphenyl)carbamate (asdescribed in WO-A 93/15,046, purity approximately 70%), and stirring wascontinued for 12 hours at approximately 25° C.

For working-up, the reaction mixture was treated with water andextracted repeatedly using tert-butyl methyl ether. After washing withwater, drying and removing the solvent, the crude product obtained fromthe combined organic phases was purified by column chromatography(eluent: a) cyclohexane/methylene chloride, b) cyclohexane/ethylacetate). This gave 0.2 g (3%) of the title compound as a pale oil.

¹ H-NMR (CDCl₃ ; δ in ppm): 2.2 (s, 3H, CH₃); 2.3 (s, 3H, CH₃); 3.75 (s,3H, OCH₃); 3.8 (s, 3H, OCH₃); 5.35 (s, 2H, OCH₂); 7.4 (m, 6H, phenyl);7.55 (m, 1H, phenyl); 7.85 (m, 2H, phenyl)

2. Preparation of ##STR11##

a) Diacetyl 0-methyloxime N-acetylhydrazone

A mixture of 6.0 g (52 mmol) of diacetyl O-methyloxime, 3.9 g (52 mmol)of acetylhydrazine and 3 drops of concentrated hydrochloric acid in 50ml of methanol was stirred overnight (approximately 12 hours) at roomtemperature (approximately 20° C). The product which had crystallizedout was isolated. The mother liquor was concentrated, product residuescrystallizing out. In total, 4.0 g (45%) of the title compound wereobtained.

¹ H-NMR (d₆ -DMSO; δ in ppm): 1.95 (s, 3H, CH₃), 2.00 (s, 3H, CH₃), 2.20(s, 3H, CH₃), 3.90 (s, 3H, OCH₃), 10.60 (s, broad, 1H, NH)

b) Title compound

A mixture of 1.85 g (11 mol) of diacetyl O-methyloxime N-acetylhydrazone(Example 2a) and 0.29 g (12 mmol) of sodium hydride in 20 ml ofdimethylformamide was stirred for 15 minutes at room temperature.

3.3 g (11 mol) of methyl N-methoxy-N-(o-bromomethylphenyl)carbamate (asdescribed in WO-A 93/15046; purity approximately 90%) were subsequentlyadded, and the mixture was stirred for approximately 1.5 hours at roomtemperature. The reaction mixture was subsequently diluted with waterand the aqueous phase was extracted three times with methyl t-butylether. The combined organic phases were washed with water, dried overmagnesium sulfate and concentrated. The residue was purified by columnchromatography (eluent: cyclohexane/methyl t-butyl ether). 1.3 g (32%)of the title compound were obtained as a yellow oil.

¹ H-NMR (CDCl₃ ; δ in ppm): 2.05 (s, 3H, CH₃), 2.10 (s, 3H, CH₃), 3.70(s, 3H, OCH₃), 3.75 (s, 3H, OCH₃), 3.95 (s, 3H, OCH₃), 5.30 (s, 2H,OCH₂), 7.40 (m, 3H, phenyl), 7.55 (m, 1H, phenyl)

                  TABLE D                                                         ______________________________________                                                                       I                                                                               #STR12##                                        -                                                                                                                 Physical data:                           No. R.sub.m XR.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 .sup.1 H NMR           ______________________________________                                                                               [ppm]                                  I1.01                                                                              --    OCH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           C.sub.6 H.sub.5                                                                    2.2; 2.3; 3.75; 3.8;                            5.35; 7.4; 7.55; 7.85                                                ______________________________________                                    

                  TABLE E                                                         ______________________________________                                          #STR13##                                                                      No.    R.sup.3                                                                              R.sup.4                                                                            R.sup.d                                                                            Re    Physical data: .sup.1 H NMR [ppm]             ______________________________________                                        I2.01                                                                              CH.sub.3                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                            2.05; 2.10; 3.70; 3.75; 3.95; 5.30;                                                 7.40; 7.55;                               ______________________________________                                    

Examples of the action against harmful fungi

The fungicidal action of the compounds of the general formula I wasdemonstrated by the experiments which follow:

The active ingredients were formulated as a 10% strength emulsion in amixture of 70% by weight of cyclohexanone, 20% by weight of Nekanil® LN(Lutensol® AP6, wetting agent having emulsifying and dispersant actionbased on ethoxylated alkylphenols) and 10% by weight of Emulphor® EL(Emulan® EL, emulsifier based on ethoxylated fatty alcohols) and dilutedwith water to give the desired concentration.

Action against Plasmopara viticola (downy mildew of grapevine)Grapevines in pots (cultivar: "Muller Thurgau") were sprayed to drippoint with the preparation of the active ingredient (rate ofapplication: 63 ppm). After 8 days, the plants were sprayed with azoospore suspension of the fungus Plasmopara viticola and kept at 20-30°C. at high atmospheric humidity, initially for 2 days. The test plantswere subsequently grown in the greenhouse for 5 days. Prior toassessment, the plants were then kept at high atmospheric humidity for16 hours. The evaluation was carried out visually.

In this test, the plants which had been treated with compound I1.01 fromTable D showed a disease level of 5% in comparison with 70% in theuntreated plants.

Action against Puccinia recondita (leaf rust of wheat)

Leaves of wheat seedlings (variety "Kanzler") were dusted with leaf rustspores (Puccinia recondita). The treated plants were incubated for 24hours at 20-22° C. and a relative atmospheric humidity of 90-95% andsubsequently treated with the aqueous preparation of the activeingredient (rate of application: 63 ppm). After a further 8 days at20-22° C. and a relative atmospheric humidity of 65-70%, the degree offungal development was determined. The evaluation was carried outvisually.

In this test, the plants which had been treated with compound I1.01 fromTable D and those with compound I2.01 from Table E showed a diseaselevel of 0% in comparison with 75% in the untreated plants.

Examples of the action against animal pests

The action of the compounds of the general formula I against animalpests was demonstrated by the experiments which follow:

The active ingredients were formulated

a. as an 0.1% strength solution in acetone or

b. as a 10% strength emulsion in a mixture of 70% by weight ofcyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wettingagent having emulsifying and dispersant action based on ethoxylatedalkylphenols) and 10% by weight of Emulphor® EL (Emulan® EL, emulsifierbased on ethoxylated fatty alcohols) and diluted to give the desiredconcentration, using acetone in the case of a. or water in the case ofb.

After the experiments had ended, in each case the lowest con wasdetermined at which 80 to 100% inhibition or mortality was still causedby the compounds in comparison with untreated controls (limit or minimalconcentration).

We claim:
 1. A phenylcarbamate of the formula I ##STR14## where thesubstituents and the index have the following meanings: R is cyano,nitro, trifluoromethyl, halogen, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy;m is 0,1 or 2, it being possible for the radicals R to be different if n is 2;R¹ is alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, and, in theevent that X is NR^(a), additionally hydrogen; X is a direct bond, 0 orNR^(a) ; R^(a) is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl orcycloalkenyl; R² is hydrogen,unsubstituted or substituted alkyl,alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, alkylcarbonylor alkoxycarbonyl; R³ and R⁴ independently of one another arehydrogen,cyano, nitro, hydroxyl, amino, halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy,C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆ -alkylamino, C₂ -C₆-alkenyl, C₂ -C₆ -alkenyloxy, C₂ -C₆ -alkenylthio, C₂ -C₆ -alkenylamino,N--C₂ -C₆ -alkenyl-N--C₁ -C₆ -alkylamino, C₂ -C₆ -alkynyl, C₂ -C₆-alkynyloxy, C₂ -C₆ -alkynylthio, C₂ -C₆ -alkynylamino, N--C₂ -C₆-alkynyl-N--C₁ -C₆ -alkylamino, it being possible for the hydrocarbonradicals of these groups to be partially or fully halogenated and/or tohave attached to them one to three of the following radicals: cyano,nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl, C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆-alkylaminocarbonyl, C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆-alkylaminothiocarbonyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylsulfoxyl,C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆-alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆ -alkylamino, C₂ -C₆-alkenyloxy, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkoxy, heterocyclyl,heterocyclyloxy, aryl, aryloxy, aryl-C₁ -C₄ -alkoxy, arylthio, aryl-C₁-C₄ -alkylthio, hetaryl, hetaryloxy, hetaryl-C₁ -C₄ -alkoxy, hetarylthioand hetaryl-C₁ -C₄ -alkylthio, it being possible for the cyclicradicals, in turn, to be partially or fully halogenated and/or to haveattached to them one to three of the following groups: cyano, nitro,hydroxyl, mercapto, amino, carboxyl, aminopcarbonyl, aminothiocarbonyl,C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆-alkylsulfoxyl, C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy,C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆-alkylamino, C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl,C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₂-C₆ -alkenyl, C₂ -C₆ -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy,arylthio, hetaryl, hetaryloxy, hetarylthio and C(═NOR^(b))--A_(n)--R^(c) ; C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkoxy, C₃ -C₆-cycloalkylthio, C₃ -C₆ -cycloalkylamino, N--C₃ -C₆ -cycloalkyl-N--C₁-C₆ -alkylamino, C₅ -C₈ -cycloalkenyl, C₅ -C₈ -cycloalkenyloxy, C₅ -C₈-cycloalkenylthio, C₅ -C₈ -cycloalkenylamino, N--C₅ -C₈-cycloalkenyl-N--C₁ -C₆ -alkylamino, heterocyclyl, heterocyclyloxy,heterocyclylthio, heterocyclylamino, N-heterocyclyl-N--C₁ -C₆-alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N--C₁ -C₆-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino,N-hetaryl-N--C₁ -C₆ -alkylamino, it being possible for the cyclicradicals to be partially or fully halogenated and/or to have attached tothem one to three of the following groups:cyano, nitro, hydroxyl,mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C₁ -C₆-alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylsulfoxyl,C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₆-haloalkoxy, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆-alkylamino, di-C₁ -C₆ -alkylamino, C₁ -C₆ -alkylaminocarbonyl, di-C₁-C₆ -alkylaminocarbonyl, C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆-alkylaminothiocarbonyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkenyloxy, benzyl,aryl-C₁ -C₆ -alkoxy, aryl, aryloxy, hetaryl, hetaryloxy, it beingpossible for the cyclic radicals of the six last-mentioned groups to bepartially or fully halogenated and/or to have attached to them a C₁ -C₆-alkyl group; C(═NOR^(b))--A_(n) --R^(c) or NR^(f) --CO--D--R^(g) ; A isoxygen, sulfur or nitrogen, the nitrogen having attached to it hydrogenor C₁ -C₆ -alkyl; D is a direct bond, oxygen or NR^(h) ; n is 0 or 1;R^(b) and R^(c) independently of one another are hydrogen or C₁ -C₆-alkyl; R^(f) is hydrogen, hydroxyl, C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂-C₆ -alkynyl, C₁ -C₆ -alkoxy, C₂ -C₆ -alkenyloxy, C₂ -C₆ -alkynyloxy, C₁-C₆ -alkoxy-C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkoxy and C₁ -C₆-alkoxycarbonyl; R^(g), R^(h) independently of one another are hydrogen,C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, C₃ -C₆ -cycloalkyl, C₃-C₆ -cycloalkenyl, aryl, aryl-C₁ -C₆ -alkyl, hetaryl and hetaryl-C₁ -C₆-alkyl; R⁵ is CR^(d) ═NOR^(e) ; R^(d) is one of the groups mentionedunder R³ ; R^(e) is hydrogen,C₁ -C₁₀ -alkyl, C₃ -C₆ -cycloalkyl, C₂ -C₁₀-alkenyl, C₂ -C₁₀ -alkynyl, C₁ -C₁₀ -alkylcarbonyl, C₂ -C₁₀-alkenylcarbonyl, C₂ -C₁₀ -alkynylcarbonyl or C₁ -C₁₀ -alkylsulfonyl, itbeing possible for these radicals to be partially or fully halogenatedand/or to have attached to them one to three of the following groups:cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl,aminothiocarbonyl, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆-alkylsulfonyl, C₁ -C₆ -alkylsulfoxyl, C₁ -C₆ -alkoxy, C₁ -C₆-haloalkoxy, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆-alkylamino, di-C₁ -C₆ -alkylamino, C₁ -C₆ -alkylaminocarbonyl, di-C₁-C₆ -alkylaminocarbonyl, C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆-alkylaminothiocarbonyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkenyloxy, C₃ -C₆-cycloalkyl, C₃ -C₆ -cycloalkyloxy, heterocyclyl, heterocyclyloxy,benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy andhetarylthio, it being possible for the last twelve groups mentioned, inturn, to be partially or fully halogenated and/or to have attached tothem one to three of the following groups: cyano, nitro, hydroxyl,mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, C₁ -C₆-alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylsulfoxyl,C₃ -C₆ -cycloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆-alkoxycarbonyl, C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆-alkylamino, C₁ -C₆ -alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl,C₁ -C₆ -alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₂-C₆ -alkenyl, C₂ -C₆ -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy,arylthio, hetaryl, hetaryloxy, hetarylthio or C(═NOR^(b))--A_(n) --R^(c); aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl orhetarylsulfonyl, it being possible for these radicals to be partially orfully halogenated and/or to have attached to them one to three of thefollowing groups:cyano, nitro, hydroxyl, mercapto, amino, carboxyl,aminocarbonyl, aminothiocarbonyl, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁-C₆ -alkylcarbonyl, C₁ -C₆ -alkylsulfonyl, C₁ -C₆ -alkylsulfoxyl, C₃ -C₆-cycloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxycarbonyl,C₁ -C₆ -alkylthio, C₁ -C₆ -alkylamino, di-C₁ -C₆ -alkylamino, C₁ -C₆-alkylaminocarbonyl, di-C₁ -C₆ -alkylaminocarbonyl, C₁ -C₆-alkylaminothiocarbonyl, di-C₁ -C₆ -alkylaminothiocarbonyl, C₂ -C₆-alkenyl, C₂ -C₆ -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl,hetaryloxy or C(═NOR^(b))--A_(n) --R^(c) ;or a salt thereof.
 2. Acompound of the formula I as claimed in claim 1 where m is
 0. 3. Acompound of the formula I as claimed in claim 1 where R¹ is methyl.
 4. Aprocess for the preparation of a compound I as claimed in claim 1 whereR³ is not halogen, which comprises reacting a benzyl derivative of theformula II ##STR15## where L¹ is a nucleophilically exchangeable leavinggroup with a carbohydrazide of the formula III

    O═CR.sup.3 --NH--N═CR.sup.4 R.sup.5                III.


5. 5. A composition suitable for controlling pests or harmful fungi,comprising a solid or liquid carrier and a compound of the generalformula I as claimed in claim
 1. 6. A method of controlling harmfulfungi, which comprises treating the fungi, or the materials, plants, thesoil or seeds to be protected against fungal infection, with aneffective amount of a compound of the general formula I as claimed inclaim
 1. 7. A method of controlling pests, which comprises treating thepests, or the materials, plants, the soil or seeds to be protected fromthem, with an effective amount of a compound of the general formula I asclaimed in claim 1.